(3R,4S)-3-[(S)-3-(4-fluorobenzyl)-piperidine-1-carbonyl]-4-[(R)-1-phenyl-ethylamino]-pyrrolidine-1-carboxylic acid tert-butyl ester → (3S,4R)-3-Amino-4-[(S)-3-(4-fluorobenzyl)-piperidine-1-carbonyl]-pyrrolidine-1-carboxylic acid tert-butyl ester

HRID 497505Notes

Reaction equation

HRID 497505 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][C@@H:11]([NH:13][C@@H](C2C=CC=CC=2)C)[C@H:10]([C:22]([N:24]2[CH2:29][CH2:28][CH2:27][C@@H:26]([CH2:30][C:31]3[CH:36]=[CH:35][C:34]([F:37])=[CH:33][CH:32]=3)[CH2:25]2)=[O:23])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>[OH-].[Pd+2].[OH-].C(O)C>[C:1]([O:5][C:6]([N:8]1[CH2:9][C@@H:10]([C:22]([N:24]2[CH2:29][CH2:28][CH2:27][C@@H:26]([CH2:30][C:31]3[CH:32]=[CH:33][C:34]([F:37])=[CH:35][CH:36]=3)[CH2:25]2)=[O:23])[C@H:11]([NH2:13])[CH2:12]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 1

HCID 69748530(3R,4S)-3-[(S)-3-(4-fluorobenzyl)-piperidine-1-carbonyl]-4-[(R)-1-phenyl-ethylamino]-pyrrolidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 69748708(3S,4R)-3-Amino-4-[(S)-3-(4-fluorobenzyl)-piperidine-1-carbonyl]-pyrrolidine-1-carboxylic acid tert-butyl esterYield 95%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 702EthanolSolvent

Procedure

(3R,4S)-3-[(S)-3-(4-fluorobenzyl)-piperidine-1-carbonyl]-4-[(R)-1-phenyl-ethylamino]-pyrrolidine-1-carboxylic acid tert-butyl ester (99 mg, 195 μmol), palladium hydroxide (20 weight % on carbon, dry basis; 40 mg) and ethanol (7 mL) were combined in a pressure bottle and shaken under hydrogen atmosphere (50-55 psig) for 20 h. The mixture was filtered through Celite, and the solids were rinsed with ethanol. The filtrate was concentrated to give the product as a glassy foam (75 mg, 95%), used without further purification.

Workup

  1. filtrationThe mixture was filtered through Celite
  2. washthe solids were rinsed with ethanol
  3. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-90e280a59ca840dead03680928d0e54a
Source dataset
uspto-grants-2005_09
Patent number
US06949546B2

Reaction notes

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