(R)-2-[(4S,5S)-3-Acetyl-4-(3,5-difluoro-benzyl)-2,2-dimethyl-oxazolidin-5-yl]-4-oxo-pyrrolidine-1-carboxylic acid tert-butyl ester → (2R,4S)-2-[(4S,5S)-3-Acetyl-4-(3,5-difluoro-benzyl)-2,2-dimethyl-oxazolidin-5-yl]-4-hydroxy-4-phenyl-pyrrolidine-1-carboxylic acid tert-butyl ester

HRID 732619Notes

Reaction equation

[C:1]1([Mg]Br)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:9]([O:13][C:14]([N:16]1[CH2:20][C:19](=[O:21])[CH2:18][C@@H:17]1[C@H:22]1[O:26][C:25]([CH3:28])([CH3:27])[N:24]([C:29](=[O:31])[CH3:30])[C@H:23]1[CH2:32][C:33]1[CH:38]=[C:37]([F:39])[CH:36]=[C:35]([F:40])[CH:34]=1)=[O:15])([CH3:12])([CH3:11])[CH3:10]>CCOCC.C(OCC)(=O)C>[C:9]([O:13][C:14]([N:16]1[CH2:20][C@@:19]([OH:21])([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH2:18][C@@H:17]1[C@H:22]1[O:26][C:25]([CH3:27])([CH3:28])[N:24]([C:29](=[O:31])[CH3:30])[C@H:23]1[CH2:32][C:33]1[CH:34]=[C:35]([F:40])[CH:36]=[C:37]([F:39])[CH:38]=1)=[O:15])([CH3:10])([CH3:11])[CH3:12]

Participants

Conditions

Temperature: 23 °C

Procedure

Add phenyl magnesium bromide (3.0 mL, 9 mmol, 3M in ether) dropwise to an ice cold solution of (R)-2-[(4S,5S)-3-acetyl-4-(3,5-difluoro-benzyl)-2,2-dimethyl-oxazolidin-5-yl]-4-oxo-pyrrolidine-1-carboxylic acid tert-butyl ester (0.40 g, 0.89 mmol) in ether (20 mL). Stir 60 minutes and warm to 23° C. Dilute with ethyl acetate and wash with saturated aqueous ammonium chloride. Purify on silica gel with dichloromethane/ethyl acetate mixtures to give the desired compound as a foam (0.19 g, 41%).

Workup

washwash with saturated aqueous ammonium chloride
customPurify on silica gel with dichloromethane/ethyl acetate

Sources & evidence

ORD record: ord-ddfe7c6c63e744ba9bc7966e63ddf1ca
Source dataset: uspto-grants-2009_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07585885B2

Reaction notes

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