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

HRID 397485Notes

Reaction equation

HRID 397485 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-04add2f1e60f4252a9ea644f682b88bf
Source dataset
uspto-grants-2003_08
Patent number
US06610701B2

Reaction notes

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