Ethyl 3-Hydroxybutyrate → Ethyl (3R)-4-cyano-3-hydroxybutanoate

HRID 1723614Notes

Reaction equation

HRID 1723614 reaction equation
OC(C)CC(OCC)=O.[C:10]([CH2:12][CH:13]([OH:20])[CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16])#[N:11]>>[C:10]([CH2:12][C@@H:13]([OH:20])[CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16])#[N:11]

Participants

3

Reactant 2

HCID 62572Ethyl 3-HydroxybutyrateHCID 4184461Ethyl 4-cyano-3-hydroxybutanoate

Product 1

HCID 2733879Ethyl (3R)-4-cyano-3-hydroxybutanoateYield 99%

Procedure

Instead of ethyl 3-hydroxybutyrate used in Example 1, ethyl 4-cyano-3-hydroxybutyrate (1%, w/v) was used as a reactant and novozyme 435 lipase was used as a biocatalyst. After reaction for 3 hours, ethyl (R)-4-cyano-3-hydroxybutyrate (99% e.e) was obtained at 57.3% conversion.

Workup

  1. customAfter reaction for 3 hours

Sources & evidence

ORD record
ord-8724202879124ff59d4e0dba56da86ac
Source dataset
uspto-grants-2009_02
Patent number
US07485452B2

Reaction notes

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