Methanol → [1-Aminomethyl-4-(4-methoxy-phenyl)-butyl]-carbamic acid tert-butyl ester

HRID 1183031Notes

Reaction equation

HRID 1183031 reaction equation
[C:1]([O:5][C:6](=[O:23])[NH:7][CH:8]([C:20](=O)[NH2:21])[CH2:9][CH2:10][CH2:11][C:12]1[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=1)([CH3:4])([CH3:3])[CH3:2].CO>C1COCC1>[C:1]([O:5][C:6](=[O:23])[NH:7][CH:8]([CH2:20][NH2:21])[CH2:9][CH2:10][CH2:11][C:12]1[CH:13]=[CH:14][C:15]([O:18][CH3:19])=[CH:16][CH:17]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 887MethanolHCID 66916855[1-Carbamoyl-4-(4-methoxy-phenyl)-butyl]-carbamic acid tert-butyl ester

Product 1

HCID 66916869[1-Aminomethyl-4-(4-methoxy-phenyl)-butyl]-carbamic acid tert-butyl ester

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of [1-carbamoyl-4-(4-methoxy-phenyl)-butyl]-carbamic acid tert-butyl ester (0.5 g, 1.48 mmol) in THF (15 mL) is treated dropwise with 1M borane-THF complex (4.47 mL, 4.47 mmol) and then heated at reflux for 2 h. After cooling to RT, MeOH (20 mL) is added and the mixture is heated again at reflux for 2 h. The solvent is removed in vacuo and the resulting oil is dissolved in DCM (10 mL) and filtered through Celite® (filter material). The filtrate is concentrated in vacuo to afford the title compound as a colourless oil. [M+H]+ 308.

Workup

  1. temperatureheated
  2. temperatureat reflux for 2 h
  3. temperaturethe mixture is heated again
  4. temperatureat reflux for 2 h
  5. customThe solvent is removed in vacuo
  6. dissolutionthe resulting oil is dissolved in DCM (10 mL)
  7. filtrationfiltered through Celite® (filter material)
  8. concentrationThe filtrate is concentrated in vacuo

Sources & evidence

ORD record
ord-a456301d59584881a4a85f9667df0c0e
Source dataset
uspto-grants-2014_03
Patent number
US08664228B2

Reaction notes

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