benzyl N-[(1S,2S)-4,4-difluoro-2-(2-methylpropane-2-sulfonamido)cyclopentyl]-N-[(1R)-1-phenylethyl]carbamate → N-[(1S,2S)-2-Amino-4,4-difluorocyclopentyl]-2-methylpropane-2-sulfonamide

HRID 1750561Notes

Reaction equation

HRID 1750561 reaction equation
[F:1][C:2]1([F:34])[CH2:6][C@H:5]([N:7]([C@@H](C2C=CC=CC=2)C)C(=O)OCC2C=CC=CC=2)[C@@H:4]([NH:26][S:27]([C:30]([CH3:33])([CH3:32])[CH3:31])(=[O:29])=[O:28])[CH2:3]1.[H][H]>CO.[OH-].[OH-].[Pd+2]>[NH2:7][C@H:5]1[CH2:6][C:2]([F:1])([F:34])[CH2:3][C@@H:4]1[NH:26][S:27]([C:30]([CH3:33])([CH3:32])[CH3:31])(=[O:29])=[O:28]

Participants

5

Reactant 2

HCID 118308276benzyl N-[(1S,2S)-4,4-difluoro-2-(2-methylpropane-2-sulfonamido)cyclopentyl]-N-[(1R)-1-phenylethyl]carbamateHCID 178418361HCID 178418361, compound

Product 1

HCID 118308227N-[(1S,2S)-2-Amino-4,4-difluorocyclopentyl]-2-methylpropane-2-sulfonamide

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

A solution of benzyl N-[(1S,2S)-4,4-difluoro-2-(2-methylpropane-2-sulfonamido)cyclopentyl]-N-[(1R)-1-phenylethyl]carbamate (2.24 g, 4.53 mmol) and palladium hydroxide on carbon (20%, 1.59 g, 2.26 mmol) in methanol (65 ml) was stirred under a balloon of hydrogen gas for 17 hours. The reaction was filtered through diatomaceous earth (commercially sold under the trade mark “Celite”) and concentrated in vacuo to afford the title compound.

Workup

  1. filtrationThe reaction was filtered through diatomaceous earth (
  2. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-3680fcba3d6a437898b7087480e0c7da
Source dataset
uspto-grants-2015_10
Patent number
US09156829B2

Reaction notes

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