Water → (4R)-tert-butyl 4-(tert-butyldimethylsilyloxy)-2-(3-fluorophenyl)pyrrolidine-1-carboxylate

HRID 513004Notes

Reaction equation

[Si:1]([O:8][C@H:9]([CH2:19][CH:20]([C:22]1[CH:27]=[CH:26][CH:25]=[C:24]([F:28])[CH:23]=1)O)[CH2:10][NH:11][C:12](=[O:18])[O:13][C:14]([CH3:17])([CH3:16])[CH3:15])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].CS(Cl)(=O)=O.O>C(Cl)Cl>[Si:1]([O:8][C@H:9]1[CH2:10][N:11]([C:12]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:18])[CH:20]([C:22]2[CH:27]=[CH:26][CH:25]=[C:24]([F:28])[CH:23]=2)[CH2:19]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Participants

Conditions

Temperature: -60 °C

Procedure

To a solution of tert-butyl (2R)-2-(tert-butyldimethylsilyloxy)-4-(3-fluorophenyl)-4-hydroxybutylcarbamate (I-2) (15.8 g, 38.2 mmol) in DCM (120 mL) at −60° C. under N2 was added TEA (16 mL, 114.6 mmol) and MsCl (3.3 mL, 42.0 mmol). The resulting mixture was stirred at −60° C. for 1 hour. The reaction was poured into water, washed with brine, dried over sodium sulfate, filtered and concentrated to yield (4R)-tert-butyl 4-(tert-butyldimethylsilyloxy)-2-(3-fluorophenyl)pyrrolidine-1-carboxylate (I-3). MS m/z 418.1 (M+23)+.

Workup

washwashed with brine
dry with materialdried over sodium sulfate
filtrationfiltered
concentrationconcentrated

Sources & evidence

ORD record: ord-198ef50ce92643bfbaa3e56936e2f268
Source dataset: uspto-grants-2015_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09102671B2

Reaction notes

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