Ethyl Acetate → (S)-5-(4-Fluoro-phenyl)-5-hydroxy-1morpholin-4-yl-pentan-1-one

HRID 1052887Notes

Reaction equation

HRID 1052887 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:20])[CH2:9][CH2:10][CH2:11][C:12]([N:14]2[CH2:19][CH2:18][O:17][CH2:16][CH2:15]2)=[O:13])=[CH:4][CH:3]=1.C(OCC)(=O)C>CO>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]([OH:20])[CH2:9][CH2:10][CH2:11][C:12]([N:14]2[CH2:15][CH2:16][O:17][CH2:18][CH2:19]2)=[O:13])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 8857Ethyl AcetateHCID 580708091-(4-Fluorophenyl)-5-(morpholin-4-yl)pentane-1,5-dione

Product 1

HCID 23636213(S)-5-(4-Fluoro-phenyl)-5-hydroxy-1morpholin-4-yl-pentan-1-one

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

As per the present invention, the ketoreductase enzyme is dissolved in buffer and to this a solution of 1-(4-Fluoro-phenyl)-5-morpholin-4-yl-pentane-1,5-dione in an alcohol solvent such as methanol is added at a temperature of 20-40° C. for 15-40 hours and monitored by HPLC. To this immiscible organic solvent such as ethyl acetate is added and (S)-5-(4-Fluoro-phenyl)-5-hydroxy-1morpholin-4-yl-pentan-1-one is isolated from organic phase.

Workup

  1. additionis added at a temperature of 20-40° C. for 15-40 hours

Sources & evidence

ORD record
ord-6e317a9f930840f9b2760d5d5097404a
Source dataset
uspto-grants-2016_07
Patent number
US09388440B2

Reaction notes

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