Asymmetric syntheses method and correlated intermediate of (R)-3-aminopiperidine (I)

A technology of aminopiperidine and synthesis method, which is applied in the chemical synthesis of -3-aminopiperidine and the field of -3-aminopiperidine, can solve the problems of high price of D-ornithine, increase the cost of industrialized production and the like, and achieves technological operation. Simple, the effect of increasing the de value
CN103588699BActive Publication Date: 2015-05-27SHANGHAI PUYI CHEM CO LTD
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Patent Information

Authority / Receiving Office
CN · China
Patent Type
Patents(China)
Current Assignee / Owner
SHANGHAI PUYI CHEM CO LTD
Publication Date
2015-05-27

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Abstract

The invention relates to an asymmetric syntheses method of (R)-3-aminopiperidine (I). The method comprises: reducing a formula (III) compound to obtain a formula (II) compound, and then removing a chiral prosthetic group and an amino protective group from the formula (II) compound to obtain (R)-3-aminopiperidine (I), wherein R is the amino protective group, and specially is C1-4 alkoxycarbonyl or benzyl removable by hydrolysis or hydrogenation. Preferably, the formula (III) compound is obtained by performing a dehydration reaction on 3-piperidone and a chiral amine (R)-1-phenylethylamine. The invention also relates to a new compound (II). The asymmetric syntheses method of (R)-3-aminopiperidine (I) is reasonable in technology and concise in route, the needed product with relatively high ee value is obtained by utilizing chiral induction, the raw material is cheap and does not need resolving, no waste isomer is discharged, and the asymmetric synthesis method is applicable to large-scale industrial production.
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Description

technical field

[0001] The present invention relates to the technical field of (R)-3-aminopiperidine, more specifically, to the technical field of chemical synthesis of (R)-3-aminopiperidine, in particular to a kind of (R)-3-aminopiperidine (I ) asymmetric synthesis method and related intermediates. Background technique

[0002] (R)-3-aminopiperidine (I) is an important pharmaceutical intermediate, mainly used to synthesize dipeptidyl peptidase-IV (DPP-IV) inhibitors, such as alogliptin (Alogliptin), which is used to Antihyperglycemic drugs such as Linagliptin. So far, there are many reports on the synthesis of (R)-3-aminopiperidine (I).

[0003]

[0004] In PCT patent application publications WO2007075630 and WO2008028654, 3-aminopyridine is used as a starting material to obtain (R)-3-aminopiperidine dihydrochloride through catalytic oxidation, resolution and salification, as shown in reaction scheme 1 . Although this method has a simple route, the catalytic hydrogen...

Claims

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