(3-Benzyloxycarbonylamino-propyl)-cyclopropylmethyl-carbamic acid tert-butyl ester → (3-Amino-propyl)-cyclopropylmethyl-carbamic acid tert-butyl ester

HRID 1795294Notes

Reaction equation

HRID 1795294 reaction equation
[C:1]([O:5][C:6](=[O:26])[N:7]([CH2:12][CH2:13][CH2:14][NH:15]C(OCC1C=CC=CC=1)=O)[CH2:8][CH:9]1[CH2:11][CH2:10]1)([CH3:4])([CH3:3])[CH3:2]>C(O)C.[Pd]>[C:1]([O:5][C:6](=[O:26])[N:7]([CH2:12][CH2:13][CH2:14][NH2:15])[CH2:8][CH:9]1[CH2:10][CH2:11]1)([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 1

HCID 21023635(3-Benzyloxycarbonylamino-propyl)-cyclopropylmethyl-carbamic acid tert-butyl ester

Product 1

HCID 21023634(3-Amino-propyl)-cyclopropylmethyl-carbamic acid tert-butyl ester

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of (3-benzyloxycarbonylamino-propyl)-cyclopropylmethyl-carbamic acid tert-butyl ester (4.2 g, 0.012 mol) in ethanol (60 ml) was stirred in the presence of palladium on carbon (10%, 0.42 g) under a hydrogen atmosphere for 2 h. Filtration through celite and concentration gave (3-amino-propyl)-cyclopropylmethyl-carbamic acid tert-butyl ester; 1H NMR (CDCl3, 400 MHz) δ 3.35 (m, 2H), 3.08 (m, 2H), 2.70 (t, 2H, J=6.8 Hz), 1.67 (m, 2H), 1.46 (s, 9H), 1.30 (bs, 2H), 0.97 (m, 1H), 0.48 (m, 2H), 0.20 (q, 2H, J=5 Hz).

Workup

  1. filtrationFiltration
  2. concentrationthrough celite and concentration

Sources & evidence

ORD record
ord-7d9f267089634dd984e83005b9e20d58
Source dataset
uspto-grants-2006_04
Patent number
US07026324B2

Reaction notes

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