Water → tert-Butyl 4-(3-aminopropyl)piperidine-1-carboxylate

HRID 1986166Notes

Reaction equation

HRID 1986166 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:20]([O:24][C:25]([N:27]1[CH2:32][CH2:31][CH:30]([CH2:33][CH2:34][CH2:35][N:36]=[N+]=[N-])[CH2:29][CH2:28]1)=[O:26])([CH3:23])([CH3:22])[CH3:21].CC#N.O>C1COCC1>[C:20]([O:24][C:25]([N:27]1[CH2:32][CH2:31][CH:30]([CH2:33][CH2:34][CH2:35][NH2:36])[CH2:29][CH2:28]1)=[O:26])([CH3:23])([CH3:22])[CH3:21]

Participants

6

Reactant 4

HCID 962WaterHCID 6342AcetonitrileHCID 11776TriphenylphosphineHCID 86625341N-Boc-4-(3-azidopropyl)piperidine

Product 1

HCID 22990164tert-Butyl 4-(3-aminopropyl)piperidine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Triphenylphosphine (0.657 g, 2.50 mmol) is added to a stirred solution of 4-(3-azido-propyl)-piperidine-1-carboxylic acid tert-butyl ester (0.560 g, 2.09 mmol) in THF (2 mL)/CH3CN (5 mL)/H2O (1 mL) and the mixture is stirred at ambient temperature for 18 hours. After concentration and subsequent chromatography purification on silica gel, eluting with 2 M NH3/MeOH in dichloromethane 0-15%, the title compound is obtained as a clear oil (0.420 g, 83% yield).

Workup

  1. concentrationAfter concentration and subsequent chromatography purification on silica gel
  2. washeluting with 2 M NH3/MeOH in dichloromethane 0-15%

Sources & evidence

ORD record
ord-34fbcc64cc274f9ba2a94b302723142a
Source dataset
uspto-grants-2009_06
Patent number
US07547691B2

Reaction notes

Loading…