2-(R)-[2-(S)-[Bis-(2-methylbenzyl)-amino]-3-(3,5-difluorophenyl)-1-(S)-hydroxypropyl]-pyrrolidine-1-carboxylic acid tert-butyl ester → (R)-tert-butyl 2-((1S,2S)-2-amino-3-(3,5-difluorophenyl)-1-hydroxypropyl)pyrrolidine-1-carboxylate

HRID 732345Notes

Reaction equation

HRID 732345 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][CH2:10][C@@H:9]1[C@@H:13]([OH:41])[C@@H:14]([N:24](CC1C=CC=CC=1C)CC1C=CC=CC=1C)[CH2:15][C:16]1[CH:21]=[C:20]([F:22])[CH:19]=[C:18]([F:23])[CH:17]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[H][H]>[Pd].CO>[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][CH2:10][C@@H:9]1[C@@H:13]([OH:41])[C@@H:14]([NH2:24])[CH2:15][C:16]1[CH:21]=[C:20]([F:22])[CH:19]=[C:18]([F:23])[CH:17]=1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 688146062-(R)-[2-(S)-[Bis-(2-methylbenzyl)-amino]-3-(3,5-difluorophenyl)-1-(S)-hydroxypropyl]-pyrrolidine-1-carboxylic acid tert-butyl esterHCID 178418361HCID 178418361, compound

Product 1

HCID 57838120(R)-tert-butyl 2-((1S,2S)-2-amino-3-(3,5-difluorophenyl)-1-hydroxypropyl)pyrrolidine-1-carboxylate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Add 2-(R)-[2-(S)-[bis-(2-methylbenzyl)-amino]-3-(3,5-difluorophenyl)-1-(S)-hydroxypropyl]-pyrrolidine-1-carboxylic acid tert-butyl ester (0.116 g, 0.205 mmol), 20% palladium on carbon (0.069 g) and methanol (3 mL) and hydrogenate at one atmosphere hydrogen gas for 18 h. Add filter agent and filter and concentrate to give the title compound as a residue (0.069 g, 94%).

Workup

  1. additionAdd
  2. filtrationfilter agent
  3. filtrationfilter
  4. concentrationconcentrate

Sources & evidence

ORD record
ord-d51390029f264f1b8057089f1927895b
Source dataset
uspto-grants-2009_09
Patent number
US07585885B2

Reaction notes

Loading…