Methyl iodide → (4R)-4-benzyl-3-[(2R)-4,4,4-trifluoro-2-methylbutanoyl]-1,3-oxazolidin-2-one

HRID 2266869Notes

Reaction equation

C[Si]([N-][Si](C)(C)C)(C)C.[Na+].[CH2:11]([C@@H:18]1[CH2:22][O:21][C:20](=[O:23])[N:19]1[C:24](=[O:31])[CH2:25][CH2:26][C:27]([F:30])([F:29])[F:28])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.I[CH3:33]>C1COCC1>[CH2:11]([C@@H:18]1[CH2:22][O:21][C:20](=[O:23])[N:19]1[C:24](=[O:31])[C@H:25]([CH3:33])[CH2:26][C:27]([F:28])([F:29])[F:30])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

Conditions

Temperature: -20 °C

Procedure

To a solution of sodium bis(trimethylsilyl)amide (57 mL, 1.0 M in THF, 57 mmol) in THF (250 mL) at −40° C. was added (4R)-4-benzyl-3-(4,4,4-trifluorobutanoyl)-1,3-oxazolidin-2-one (15.60 g, 51.78 mmol) in THF (250 mL) dropwise over 15 min. After 1 h, iodomethane (4.2 mL, 67 mmol) was added. After 3 h, the reaction mixture was warmed to −20° C. for about 20 min. The mixture was quenched with saturated aqueous ammonium chloride (NH4Cl) (300 mL) and then extracted with EtOAc (2×300 mL), dried using Na2SO4, and concentrated. Flash chromatography (eluent: 1:9 EtOAc-hexane) provided (4R)-4-benzyl-3-[(2R)-4,4,4-trifluoro-2-methylbutanoyl]-1,3-oxazolidin-2-one (12.04 g, 74%) as a colorless oil. [a]D25=−98.68° (c=1% SOLUTION, DMSO). Mass Spectrum (+EI): 315 (M+H)+.

Workup

waitAfter 3 h
customThe mixture was quenched with saturated aqueous ammonium chloride (NH4Cl) (300 mL)
extractionextracted with EtOAc (2×300 mL)
customdried
concentrationconcentrated

Sources & evidence

ORD record: ord-4a71a5b7493e480bac146dc0d5212f36
Source dataset: uspto-grants-2010_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07858658B2

Reaction notes

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