tert-Butyl (3R)-3-(hydroxymethyl)pyrrolidine-1-carboxylate → (R)-tert-Butyl 3-(fluoromethyl)-pyrrolidine-1-carboxylate

HRID 1445778Notes

Reaction equation

HRID 1445778 reaction equation
[F:1][C@H]1CCN(C(OC(C)(C)C)=O)C1.[C:14]([N:21]1[CH2:25][CH2:24][C@@H:23]([CH2:26]O)[CH2:22]1)([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15].COCCN(S(F)(F)F)CCOC>ClCCl>[F:1][CH2:26][C@@H:23]1[CH2:24][CH2:25][N:21]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:22]1

Participants

5

Reactant 3

HCID 1514340tert-Butyl (3R)-3-(hydroxymethyl)pyrrolidine-1-carboxylateHCID 2734690(Bis(2-methoxyethyl)amino)sulfur trifluorideHCID 18453464tert-Butyl (3S)-3-fluoropyrrolidine-1-carboxylate

Product 1

HCID 58951460(R)-tert-Butyl 3-(fluoromethyl)-pyrrolidine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Prepare using the method of Intermediate 48 with (R)-N-Boc-pyrrolidine-3-methanol (0.50 g, 2.48 mmol), [bis(2-methoxyethyl)amino]sulfur trifluoride (0.55 mL, 2.98 mmol) and anhydrous dichloromethane (2.5 mL) to give the title compound as a colourless oil (0.34 g): MS (m/e): 226 (M+23).

Workup

  1. customPrepare

Sources & evidence

ORD record
ord-7c4b8b66d23646699386e2d25400c06e
Source dataset
uspto-grants-2010_02
Patent number
US07666871B2

Reaction notes

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