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Preparation method for synthesizing N-Boc-trans-1, 4-cyclohexanediamine

A cyclohexanediamine, n-boc- technology, applied in the field of organic compound preparation, can solve the problems of inability to judge the complete reaction, harsh reaction conditions, many reaction by-products, etc., and achieves mild reaction conditions, simple purification, and few by-products. Effect

Inactive Publication Date: 2022-08-02
泽升科技(广州)有限公司 +1
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0003]The existing N-Boc-trans-1,4-cyclohexanediamine is directly synthesized by trans-1,4-cyclohexanediamine and Boc anhydride , Boc anhydride will have multiple substitutions, many reaction by-products, and low purity; another method is to protect the 1-position amino group with an equivalent amount of benzophenone for trans-1,4-cyclohexanediamine, and then Under conditions, react with Boc anhydride; then react in alcohol solvent under the catalysis of boron trifluoride ether to obtain N-Boc-trans-1,4-cyclohexanediamine, but this method requires strict control of diphenyl The amount of ketone is used, and it is impossible to judge whether the reaction is complete, and the reaction conditions are harsh

Method used

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preparation example Construction

[0029] The embodiment of the present invention discloses a preparation method for synthesizing N-Boc-trans-1,4-cyclohexanediamine, comprising the following steps:

[0030] The first step is to react trans-1,4-cyclohexanediamine with acid chloride under the action of catalyst 1 to obtain intermediate 1;

[0031] In the second step, intermediate 1 is combined with (Boc) 2 O reacts in the presence of acid binding agent to obtain intermediate 2;

[0032] In the third step, the intermediate 2 is reacted under the conditions of catalyst 2 and hydrogen to obtain N-Boc-trans-1,4-cyclohexanediamine.

[0033] As an embodiment of the present invention, in the first step, the acid chloride is selected from acetyl chloride, propionyl chloride, butyryl chloride, tert-butyryl chloride, isobutyryl chloride, valeryl chloride, isovaleryl chloride, hexanoyl chloride, isohexanoyl chloride, heptanoyl chloride, isoheptanoyl chloride Acid chloride, octanoyl chloride, isooctanoyl chloride, nonanoyl...

Embodiment 1

[0104] A preparation method for synthesizing N-Boc-trans-1,4-cyclohexanediamine, the synthetic route is as follows:

[0105] .

[0106] A preparation method for synthesizing N-Boc-trans-1,4-cyclohexanediamine, comprising the following synthesis steps:

[0107] The first step: add 100g trans-1,4-cyclohexanediamine and 103.91g pyridine into 500mL dichloromethane, add 69.44g acetyl chloride dropwise to the system at 0°C, and then react at room temperature for 6h, the reaction is over After the solvent was spin-dried, dissolved in ethyl acetate, and washed with weak acid conditions; the organic phase was dried, evaporated and purified to obtain 128.61 g of intermediate 1 with a yield of 94.7%; 1 HNMR (400MHz, DMSO): 8.08 (s, 1H), 5.17 (s, 2H), 3.59 (m, 1H), 2.62 (m, 1H), 2.30 (m, 2H), 1.90 (s, 3H), 1.76 -1.54 (m, 8H);

[0108] Step 2: Combine 128.61g of Intermediate 1 with 188.65g of (Boc) 2 O was added to 500 mL of 1,4-dioxane, and under nitrogen protection, a saturated aqu...

Embodiment 2

[0111] A preparation method for synthesizing N-Boc-trans-1,4-cyclohexanediamine, the synthetic route thereof is the same as that in Embodiment 1.

[0112] A preparation method for synthesizing N-Boc-trans-1,4-cyclohexanediamine, comprising the following synthesis steps:

[0113] The first step: 100g trans-1,4-cyclohexanediamine and 159.32g pyridine were added to 500mL dichloromethane, 75.63g acetyl chloride was added dropwise to the system at 0°C, and then reacted at room temperature for 6h, the reaction was over The solvent was then spin-dried, dissolved in dichloromethane, and washed with weak acid conditions; the organic phase was dried, evaporated and purified to obtain 130.94 g of intermediate 1 with a yield of 95.7%;

[0114] Step 2: Combine 130.94g of Intermediate 1 with 201.20g of (Boc) 2 O was added to 500 mL of 1,4-dichloromethane, and the saturated aqueous solution prepared with 73.77 g of NaOH was slowly added to the system, and the reaction was carried out at roo...

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Abstract

The invention discloses a preparation method for synthesizing N-Boc-trans-1, 4-cyclohexanediamine, and belongs to the technical field of organic compound preparation, the preparation method comprises the following steps: 1, reacting trans-1, 4-cyclohexanediamine with acyl chloride or sulfonyl chloride under the action of a catalyst 1 to obtain an intermediate 1; 2, reacting the intermediate 1 with (Boc) 2O in the presence of an acid-binding agent to obtain an intermediate 2; and 3, carrying out a reaction on the intermediate 2 in the presence of a catalyst 2 and hydrogen to obtain N-Boc-trans-1, 4-cyclohexanediamine. According to the preparation method, trans-1, 4-cyclohexanediamine is adopted as a raw material, one amino group in trans-1, 4-cyclohexanediamine is protected, the proportion of a protective agent to 1: 1 does not need to be strictly controlled, multi-site substitution is avoided, byproducts are few, and purification is simple and convenient; the preparation method is mild in reaction condition, high in yield, high in purity and good in economic benefit.

Description

technical field [0001] The invention belongs to the technical field of organic compound preparation, in particular to a preparation method for synthesizing N-Boc-trans-1,4-cyclohexanediamine. Background technique [0002] N-Boc-trans-1,4-cyclohexanediamine is widely used as a pharmaceutical raw material, and its downstream products include intermediates for preparing kinase inhibitors or intermediates for inhibiting poly ADP ribosylated proteins; its upstream products, trans- 1,4-Cyclohexanediamine, as a chiral organic amine with symmetrical structure of heterocyclic ring, is widely used in the field of medicine. It is an important pharmaceutical intermediate and plays an important role in the preparation of medicine. Trans-1,4-cyclohexanediamine has two amino groups, and one of the amino groups usually needs to be protected in the reaction to carry out the subsequent reaction. [0003] Existing N-Boc-trans-1,4-cyclohexanediamine is directly synthesized by trans-1,4-cyclohe...

Claims

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Application Information

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IPC IPC(8): C07C269/06C07C271/24
CPCC07C269/06C07C269/04C07C231/02C07C303/40C07C303/38C07C2601/14C07B2200/07C07C271/24C07C233/41C07C311/20C07C311/13Y02P20/584Y02P20/55
Inventor 刘银辉张吉
Owner 泽升科技(广州)有限公司
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