Triethylamine → (trans)-Benzyl 3-fluoro-4-(methylsulfonyloxy)pyrrolidine-1-carboxylate

HRID 1095679Notes

Reaction equation

[F:1][C@H:2]1[C@H:6]([OH:7])[CH2:5][N:4]([C:8]([O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[O:9])[CH2:3]1.[CH3:18][S:19](Cl)(=[O:21])=[O:20].C(N(CC)CC)C>ClCCl>[F:1][C@H:2]1[C@H:6]([O:7][S:19]([CH3:18])(=[O:21])=[O:20])[CH2:5][N:4]([C:8]([O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[O:9])[CH2:3]1

Participants

Conditions

Temperature: 0 °C

Procedure

(trans)-Benzyl 3-fluoro-4-hydroxypyrrolidine-1-carboxylate (2.0 g, 8.36 mmol) was added to dichloromethane and cooled to 0° C. Methanesulfonyl chloride (1.30 mL, 16.7 mmol) and triethylamine (2.3 mL, 16.7 mmol) were sequentially added, and the reaction was allowed to warm to ambient temperature overnight under vigorous stirring. The following day, additional dichloromethane was added, and the reaction mixture was washed with a saturated solution of NaHCO3. The combined organic layers were dried over MgSO4, filtered and evaporated. The crude oil was purified on silica gel using ethyl acetate and hexane to produce 2.0 g (70% isolated yield) of the desired product as an oil.

Workup

temperatureto warm to ambient temperature overnight under vigorous stirring
washthe reaction mixture was washed with a saturated solution of NaHCO3
dry with materialThe combined organic layers were dried over MgSO4
filtrationfiltered
customevaporated
customThe crude oil was purified on silica gel
customto produce

Sources & evidence

ORD record: ord-03d21310852c45dfb7e2bb5a8a5c42f5
Source dataset: uspto-grants-2012_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08138181B2

Reaction notes

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