Triphenylphosphine → Tert-butyl 2-(aminomethyl)-4-chlorobenzylcarbamate

HRID 1058337Notes

Reaction equation

HRID 1058337 reaction equation
[N:1]([CH2:4][C:5]1[CH:19]=[C:18]([Cl:20])[CH:17]=[CH:16][C:6]=1[CH2:7][NH:8][C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[N+]=[N-].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1COCC1.O>[NH2:1][CH2:4][C:5]1[CH:19]=[C:18]([Cl:20])[CH:17]=[CH:16][C:6]=1[CH2:7][NH:8][C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12]

Participants

5

Reactant 2

HCID 11776TriphenylphosphineHCID 12052445Tert-butyl 2-(azidomethyl)-4-chlorobenzylcarbamate

Product 1

HCID 11149921Tert-butyl 2-(aminomethyl)-4-chlorobenzylcarbamate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of tert-butyl 2-(azidomethyl)-4-chlorobenzylcarbamate (10.9 g, 36.73 mmol) in THF (60 ml) and water (6 ml) was added triphenylphospine (10.59 g, 40.40 mmol). The reaction was heated to 65 C and stirred overnight at room temperature. The reaction was concentrated in vacuo and flashed with 4% (10% NH4OH/MeOH)/dichlor-omethane. A second purification using silica gel column chromatography with a careful gradient of 3 to 5% (10% NH4OH/MeOH)/dichloro methane gave the title compound.

Workup

  1. temperatureThe reaction was heated to 65 C
  2. concentrationThe reaction was concentrated in vacuo
  3. customA second purification

Sources & evidence

ORD record
ord-3b9fe27af65944ab9dbfb13a7a6a2798
Source dataset
uspto-grants-2003_02
Patent number
US06515011B2

Reaction notes

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