p-Toluenesulfonic acid monohydrate → (3R)-3-(Fluoromethyl)pyrrolidine 4-methylbenzenesulfonate

HRID 1445779Notes

Reaction equation

HRID 1445779 reaction equation
O.[C:2]1([CH3:12])[CH:7]=[CH:6][C:5]([S:8]([OH:11])(=[O:10])=[O:9])=[CH:4][CH:3]=1.[F:13][CH2:14][C@@H:15]1[CH2:19][CH2:18][N:17](C(OC(C)(C)C)=O)[CH2:16]1>C(O)C>[CH3:12][C:2]1[CH:3]=[CH:4][C:5]([S:8]([OH:11])(=[O:10])=[O:9])=[CH:6][CH:7]=1.[F:13][CH2:14][C@@H:15]1[CH2:19][CH2:18][NH:17][CH2:16]1

Participants

4

Reactant 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 58951460(R)-tert-Butyl 3-(fluoromethyl)-pyrrolidine-1-carboxylate2×

Product 1

HCID 86614638(3R)-3-(Fluoromethyl)pyrrolidine 4-methylbenzenesulfonateYield 81.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Prepare using the method of Intermediate 49 with p-toluenesulfonic acid monohydrate (0.304 g, 1.87 mmol), tert-butyl (3R)-3-(fluoromethyl)pyrrolidine-1-carboxylate (See Intermediate 56) (0.325 g, 1.87 mmol) and ethanol (2 mL) to give the title compound as a white solid (0.421 g): MS (m/e): 104 (M+1).

Workup

  1. customPrepare

Sources & evidence

ORD record
ord-f742bd614d5b4c15947e553b4518bc72
Source dataset
uspto-grants-2010_02
Patent number
US07666871B2

Reaction notes

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