Tert-butyl n-[1-(azidomethyl)undecyl]-carbamate → t-butyl N-(1-aminododecan-2-yl) carbamate

HRID 970302Notes

Reaction equation

HRID 970302 reaction equation
[N:1]([CH2:4][CH:5]([NH:16][C:17](=[O:23])[O:18][C:19]([CH3:22])([CH3:21])[CH3:20])[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH3:15])=[N+]=[N-]>[Pd].CO>[NH2:1][CH2:4][CH:5]([NH:16][C:17](=[O:23])[O:18][C:19]([CH3:22])([CH3:21])[CH3:20])[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH3:15]

Participants

4

Reactant 1

HCID 91612995Tert-butyl n-[1-(azidomethyl)undecyl]-carbamate

Product 1

HCID 87843007t-butyl N-(1-aminododecan-2-yl) carbamateYield 92.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Palladium catalyst (10% on carbon, 10.0 mg) was added in one portion to a solution of tert-butyl N-[1-(azidomethyl)undecyl]-carbamate 63 (100 mg, 0.282 mmol) in abs. methanol (5 ml) under a hydrogen atmosphere. The solution was allowed to stir for 12 hours. The catalyst was subsequently filtered off, and the solvent evaporated to give 64 (78 mg, 84%).

Workup

  1. filtrationThe catalyst was subsequently filtered off
  2. customthe solvent evaporated

Sources & evidence

ORD record
ord-2d0eb11366644590a0c8c9fd1e987b95
Source dataset
uspto-grants-2007_12
Patent number
US07312194B2

Reaction notes

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