Reaktion #533303

ord-7537f17088eb4c73b05e3fe906f82c82

Reaktionsgleichung

CC1CN([C@H](C)c2ccccc2)C[C@@]1(CF)NC(=O)OC(C)(C)C
(3S)-3-(tert-butoxycarbonylamino)-3-fluoromethyl-4-methyl-1-[(1R)-1-phenylethyl]pyrrolidine
→
CC1CNC[C@@]1(CF)NC(=O)OC(C)(C)C
crude title compound
CC1CNC[C@@]1(CF)NC(=O)OC(C)(C)C
(3S)-3-(tert-Butoxycarbonylamino)-3-fluoromethyl-4-methylpyrrolidine

Edukte

CC1CN([C@H](C)c2ccccc2)C[C@@]1(CF)NC(=O)OC(C)(C)C
(3S)-3-(tert-butoxycarbonylamino)-3-fluoromethyl-4-methyl-1-[(1R)-1-phenylethyl]pyrrolidine

Reagenzien

[C].[Pd]
palladium-carbon

Lösungsmittel

[H][H]
hydrogen
CCO
ethanol

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    SonstigeAfter removing the catalyst
  2. 2
    Filtrationby filtration
  3. 3
    Sonstigethe solvent was removed by distillation under reduced pressure

Vorschrift

To a solution of (3S)-3-(tert-butoxycarbonylamino)-3-fluoromethyl-4-methyl-1-[(1R)-1-phenylethyl]pyrrolidine (200 mg, 0.594 mmol) in ethanol (12 mL) was added 10% palladium-carbon catalyst (containing 52.8% water, 200 mg), and the suspension was stirred in an oil bath at 40° C. for 2 hours in hydrogen gas atmosphere. After removing the catalyst by filtration, the solvent was removed by distillation under reduced pressure to obtain 150 mg (quantitative) of the crude title compound as a white solid.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US08476429B2uspto-grants-2013_07