p-Toluenesulfonic acid monohydrate → (3S)-3-Fluoropyrrolidine 4-methylbenzenesulfonate

HRID 1445772Notes

Reaction equation

HRID 1445772 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][C@H:14]1[CH2:18][CH2:17][N:16](C(OC(C)(C)C)=O)[CH2:15]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][C@H:14]1[CH2:18][CH2:17][NH:16][CH2:15]1

Participants

4

Reactant 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 18453464tert-Butyl (3S)-3-fluoropyrrolidine-1-carboxylate2×

Product 1

HCID 86614633(3S)-3-Fluoropyrrolidine 4-methylbenzenesulfonateYield 94.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Add p-toluenesulfonic acid monohydrate (0.50 g, 2.64 mmol) to tert-butyl (3S)-3-fluoropyrrolidine-1-carboxylate (See Intermediate 48) (0.50 g, 2.64 mmol) in ethanol (5 mL) at room temperature. Stir the resulting solution overnight. Concentrate the reaction mixture in vacuo to remove solvent and bi-products to give the title compound as an off-white solid (0.65 g): MS (m/e): 90 (M+1).

Workup

  1. concentrationConcentrate the reaction mixture in vacuo
  2. customto remove solvent and bi-products

Sources & evidence

ORD record
ord-4ef1691e546240c894db82db09b1382f
Source dataset
uspto-grants-2010_02
Patent number
US07666871B2

Reaction notes

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