Cesium fluoride → (R)-3-benzyl-5-methoxymethyloxazolidin-2-one

HRID 650261Notes

Reaction equation

[CH2:1]([NH:8][C:9]([O:11][CH2:12][CH3:13])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[F-].[Cs+].[CH3:16][O:17][CH2:18][C@H]1COC(=O)O1>CS(C)=O>[CH2:1]([N:8]1[CH2:13][C@H:12]([CH2:16][O:17][CH3:18])[O:11][C:9]1=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 140 °C

Procedure

Benzylurethane (15.0 g, 83.9 mmol) was dissolved in dimethyl sulfoxide (40 mL), and thereto were added cesium fluoride (1.16 g, 7.63 mmol) and (S)-4-methoxymethyl-1,3- dioxolan-2-one (10.0 g, 76.3 mmol, optical purity 98.4%ee), in order. The mixture was stirred for 28 hours at 140° C. under an atmosphere of argon. After filtering off the insoluble materials, the filtrate was condensed in vacuo, and the residue was purified by silica gel chromatography to give the subject (R)-3-benzyl-5-methoxymethyloxazolidin-2-one (14.1 g, yield 83.5%, optical purity 98.2%ee).

Workup

filtrationAfter filtering off the insoluble materials
customcondensed in vacuo
customthe residue was purified by silica gel chromatography

Sources & evidence

ORD record: ord-15b137d2ed9749bfbcbe80f540de4008
Source dataset: uspto-grants-2001_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06271388B1

Reaction notes

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