1-Methyl-3,3-diphenyltetrahydro-3H-pyrrolo[1,2-c][1,3,2]oxazaborole → 3-(5-Hydroxy-5-phenylpentanoyl)-4-phenyl-1,3-oxazolidin-2-one

HRID 2300702Notes

Reaction equation

HRID 2300702 reaction equation
CB1N2CCCC2C(C2C=CC=CC=2)(C2C=CC=CC=2)O1.[O:22]=[C:23]1[N:27]([C:28](=[O:40])[CH2:29][CH2:30][CH2:31][C:32]([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)=[O:33])[CH:26]([C:41]2[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=2)[CH2:25][O:24]1>>[OH:33][CH:32]([C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)[CH2:31][CH2:30][CH2:29][C:28]([N:27]1[CH:26]([C:41]2[CH:42]=[CH:43][CH:44]=[CH:45][CH:46]=2)[CH2:25][O:24][C:23]1=[O:22])=[O:40]

Participants

3

Reactant 2

HCID 5510901-Methyl-3,3-diphenyltetrahydro-3H-pyrrolo[1,2-c][1,3,2]oxazaboroleHCID 183745891-(2-Oxo-4-phenyloxazolidin-3-yl)-5-phenylpentane-1,5-dione

Product 1

HCID 183745813-(5-Hydroxy-5-phenylpentanoyl)-4-phenyl-1,3-oxazolidin-2-one

Procedure

Under argon and at a temperature between 0° and −5° C., 5 g of 1-(2-oxo-4-phenyloxazolidin-3-yl)-5-phenylpentane-1,5-dione in 20 ml of dichloromethane are slowly, over a period of about 3 hours, added to a solution of 1.5 ml of boron-dimethylsulfide-complex in 25 ml of dichloromethane. The mixture is stirred at the same temperature for another 2 hours, the reaction being monitored by thin-layer chromatography. After the reaction has ended, 2 ml of methanol and 1.5 ml of 35 percent strength hydrogen peroxide solution and 1.1 ml of 3N sulfuric acid are added at below 0° C., and the mixture is stirred at room temperature for another 15 min. After phase separation, the organic phase is washed successively with 2N sulfuric acid, 5% strength sodium bisulfite solution and 10 percent strength sodium chloride solution and then dried and concentrated. After chromatography (SiO2, ethyl acetate/n-heptane=1:1, the product of molecular weight 339.4 (C20H21NO4); MS (DCl+): 322 (M+H+−H2O); (ESI+):403 (M+Na++CH3CN), 362 (M+Na+) is obtained. By adding optically active 1-methyl-3,3-diphenyltetrahydropyrrolo[1,2-c][1,3,2]oxazaborole (S or R, 0.75 ml) at from 0° to −5° C. to the reaction mixture prior to the addition of 1-(2-oxo-4-phenyloxazolidin-3-yl)-5-phenylpentane-1,5-dione, by the same route, 3 is obtained in diastereomerically enriched form.

Workup

  1. customby the same route, 3 is obtained in diastereomerically enriched form

Sources & evidence

ORD record
ord-4eed129bd7dd416fabbab0cc9ac5b69e
Source dataset
uspto-grants-2002_12
Patent number
US06498156B2

Reaction notes

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