1,8-Diazabicyclo(5.4.0)undec-7-ene → Tert-butyl 2-(aminomethyl)-4-chlorobenzylcarbamate

HRID 397484Notes

Reaction equation

HRID 397484 reaction equation
[Cl:1][C:2]1[CH:16]=[CH:15][C:5]([CH2:6][NH:7][C:8](=[O:14])[O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[C:4]([CH2:17]O)[CH:3]=1.C1C=CC(P([N:33]=[N+]=[N-])(C2C=CC=CC=2)=O)=CC=1.C1CCN2C(=NCCC2)CC1>C1COCC1>[NH2:33][CH2:17][C:4]1[CH:3]=[C:2]([Cl:1])[CH:16]=[CH:15][C:5]=1[CH2:6][NH:7][C:8](=[O:14])[O:9][C:10]([CH3:13])([CH3:12])[CH3:11]

Participants

5

Reactant 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 199401P,P-Diphenylphosphinic azideHCID 12052444Tert-butyl 4-chloro-2-(hydroxymethyl)benzylcarbamate

Product 1

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

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of tert-butyl 4-chloro-2-(hydroxymethyl)benzylcarbamate (10 g, 36.8 mmol) in anhydrous THF (100 ml) was added DPPA (8.3 ml, 38.6 mmol) and DBU (5.79 ml, 38.6 mmol). The mixture was stirred overnight and then was partitioned between ethyl acetate and water. The organic layer was washed with brine, and was concentrated in vacuo to a crude oil (14.6 g). Purification was accomplished by silica gel chromatography, eluting a gradient of ethyl acetate-hexane (10, 15, 20, 25, 50%) to give tert-butyl 2-(aminomethyl)-4-chlorobenzylcarbamate.

Workup

  1. customwas partitioned between ethyl acetate and water
  2. washThe organic layer was washed with brine
  3. concentrationwas concentrated in vacuo to a crude oil (14.6 g)
  4. customPurification
  5. washeluting a gradient of ethyl acetate-hexane (10, 15, 20, 25, 50%)

Sources & evidence

ORD record
ord-5856e21ad03647968f2456be76a3da00
Source dataset
uspto-grants-2003_08
Patent number
US06610701B2

Reaction notes

Loading…