tert-Butyl (3S)-3-hydroxypyrrolidine-1-carboxylate → tert-Butyl (3R)-3-fluoropyrrolidine-1-carboxylate

HRID 1445773Notes

Reaction equation

HRID 1445773 reaction equation
[F:1][C@H:2]1[CH2:6][CH2:5][N:4]([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[CH2:3]1.C(N1CC[C@H](O)C1)(OC(C)(C)C)=O.COCCN(S(F)(F)F)CCOC>ClCCl>[F:1][C@@H:2]1[CH2:6][CH2:5][N:4]([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[CH2:3]1

Participants

5

Reactant 3

HCID 854055tert-Butyl (3S)-3-hydroxypyrrolidine-1-carboxylateHCID 2734690(Bis(2-methoxyethyl)amino)sulfur trifluorideHCID 18453464tert-Butyl (3S)-3-fluoropyrrolidine-1-carboxylate

Product 1

HCID 40430177tert-Butyl (3R)-3-fluoropyrrolidine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Prepare using the method of Intermediate 48 with N-Boc-(S)-(+)-3-pyrrolidinol (0.50 g, 2.67 mmol), [bis(2-methoxyethyl)amino]sulfur trifluoride (0.59 mL, 3.20 mmol) and anhydrous dichloromethane (4 mL) to give the title compound as a colourless oil (0.36 g): MS (m/e): 212 (M+23).

Workup

  1. customPrepare

Sources & evidence

ORD record
ord-0b2be6b0167a49a795e99b18636c7920
Source dataset
uspto-grants-2010_02
Patent number
US07666871B2

Reaction notes

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