N-(2-Azido-2-methylcyclopentyl)-4-methylbenzene-1-sulfonamide → N-(2-Amino-2-methylcyclopentyl)-4-methylbenzene-1-sulfonamide

HRID 1750503Notes

Reaction equation

HRID 1750503 reaction equation
[N:1]([C:4]1([CH3:20])[CH2:8][CH2:7][CH2:6][CH:5]1[NH:9][S:10]([C:13]1[CH:18]=[CH:17][C:16]([CH3:19])=[CH:15][CH:14]=1)(=[O:12])=[O:11])=[N+]=[N-].[H][H]>CO.[Pd]>[NH2:1][C:4]1([CH3:20])[CH2:8][CH2:7][CH2:6][CH:5]1[NH:9][S:10]([C:13]1[CH:14]=[CH:15][C:16]([CH3:19])=[CH:17][CH:18]=1)(=[O:12])=[O:11]

Participants

5

Reactant 2

HCID 118024623N-(2-Azido-2-methylcyclopentyl)-4-methylbenzene-1-sulfonamideHCID 178418361HCID 178418361, compound

Product 1

HCID 118024789N-(2-Amino-2-methylcyclopentyl)-4-methylbenzene-1-sulfonamide

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of N-(2-azido-2-methylcyclopentyl)-4-methylbenzene-1-sulfonamide (52.0 g, 176.87 mmol) in methanol (1100 ml) was added palladium on carbon (10% wt, 10.0 g). The reaction mixture was stirred at room temperature under a balloon of hydrogen gas for 12 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-aca512afb69d4c2fa58de20e4716cd72
Source dataset
uspto-grants-2015_10
Patent number
US09156829B2

Reaction notes

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