Propellane derivates and synthesis

A technology of alkyl compounds, applied in the field of synthetic organic chemistry, which can solve the problems of reagent availability and cost constraints for commercial use

Pending Publication Date: 2021-09-03
RECURIUM IP HLDG LLC
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In short, the commercial use of BCP is limited by the availability and cost of reagents

Method used

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  • Propellane derivates and synthesis
  • Propellane derivates and synthesis
  • Propellane derivates and synthesis

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0139] Example 1: General process

[0140] Preparation of anhydrous EtOH, anhydrous MeOH or anhydrous MeOH and anhydrous ET 2 O ~ 2: 1 mixture of Fe (ACAC) 3 Solution (30 mol% or 50 mol%) and in N 2 The mixture was stirred for 2 min. Add [1.1.1] rampane (1 equivalent, for dissolving in etha) 2 O solution) and suitable reagents (1.2-3 equivalents) capable of providing all or part of the substituent, then add phsih 3 (1.0-1.5 equivalents). After stirring at room temperature (RT) overnight, a mixture containing the product was concentrated to give the compound, which can be further purified by flash chromatography on silica gel, or non-separated or non-purified product, continued to treat the product to produce a corresponding derivative .

Embodiment 2

[0141] Example 2: Double ring [1.1.1] pentane-1-methitrile:

[0142]

[0143] According to the general process, 4-methylbenzenesulfin cyanocyanide (TSCN) is used as a suitable reagent capable of providing all or some of the substituents (1.1.1] pentane-1-methitrile. 1 H NMR (400MHz, MeOH-D 4 Δ2.40 (S, 1H), 2.31 (S, 6H).

Embodiment 3

[0144] Example 3: Double ring [1.1.1] pentane-1-ylomethyme

[0145]

[0146] By dissolving the double ring [1.1.1] pentane-1-methitrile in anhydrous ET 2 O (0.090 m) was prepared for bicyclic [1.1.1] pentane-1-ylomethynine and cooled to 0 ° C. The LaH solution (5.3 equivalent) dissolved in THF was added dropwise by stirring. After 30 min, the solution was quenched at 0 ° C by adding EtOAc (2 mL). The mixture was concentrated to 30% of its original volume and loaded to Si-p-p-toluenesulfonic acid resin column. Rinse the column with MeOH, then use 1N NH dissolved in MeOH 3 Element elution compound. The solution was concentrated to 10% of its original volume, and then acidified with 4 NHCl dissolved in dioxane and evaporated to give a double ring [1.1.1] pentane-1-ylmethylamine. 1 H NMR (400MHz, MeOH-D 4 Δ2.97 (S, 2H), 2.57 (S, 1H), 1.90 (S, 6H); LC / MS (APCI) M / Z 98.1 [C 6 Hide 11 N + h] + .

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Abstract

Disclosed herein are compounds of the general Formula (I), and methods of synthesizing substituted bicyclo[1.1.1]pentanes. The synthetic methods described herein use a [1.1.1]propellane, a Group VIII transition metal compound, a hydride source and a reagent that can contribute a substituent to form a substituted bicycIo[1.1.1]pentane, such as a compound of the general Formula (I).

Description

[0001] The present application is a score application for the presentation of China Patent Application No. 2015800, 200861.9, filed on March 5, 2015. [0002] Incorporate by reference to any priority application [0003] Based on 37CFR 1.57, as well as Regulations 4.18 and 20.6, based on the proposed foreign priority statement or domestic priority statement (for example, in any of the application data sheets or requests submitted in the application) and all applications Enter this article. Technical field [0004] The present disclosure relates to synthesis organic chemistry, and specifically, based on [1.1.1] - bicyclopentane compound (bolthane derivative) and its synthesis. Background technique [0005] In synthetic organic chemistry, new types of small organic molecules for use as reagents are significantly required. Although it is estimated that there is 10 60 The possible carbon-containing small molecule, but only the very small portion can be effectively and efficiently synt...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C211/19C07C229/28C07C271/22
CPCC07C255/46C07C255/64C07C271/22C07C211/35C07C229/28C07C247/14C07C251/42C07C45/44C07C2602/38C07D249/06C07C47/347C07C253/30C07C253/32C07F15/02C07F7/0896C07C209/48C07C31/137C07C29/00C07C209/26C07C211/19C07C227/04C07C249/04C07C251/40C07C253/00C07C255/31C07C255/47C07C269/00
Inventor 凯文·杜安·邦克
Owner RECURIUM IP HLDG LLC
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