Borane → HCID 67087024, compound

HRID 2365521Notes

Reaction equation

HRID 2365521 reaction equation
[C:1]([O:5][C:6](=[O:24])[NH:7][CH2:8][CH2:9][NH:10][C:11](=O)[CH2:12][CH2:13][CH2:14][C:15]1[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=1)([CH3:4])([CH3:3])[CH3:2].B>C1COCC1>[C:1]([O:5][C:6](=[O:24])[NH:7][CH2:8][CH2:9][NH:10][CH2:11][CH2:12][CH2:13][CH2:14][C:15]1[CH:16]=[CH:17][C:18]([O:21][CH3:22])=[CH:19][CH:20]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 6331BoraneHCID 49029420HCID 49029420, compound

Product 1

HCID 67087024HCID 67087024, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of {2-[4-(4-methoxy-phenyl)-butyrylamino]-ethyl}-carbamic acid tert-butyl ester (6 g, 17.88 mmol) in dry THF (60 ml) under an inert atmosphere of Argon is treated carefully with borane.THF complex (53.88 ml, 1M Borane in THF). The reaction mixture is heated at reflux for 2 hours and then allowed to cool to room temperature overnight. The mixture is quenched by addition of MeOH and then heated to 70° C. for a further 2 hours. After cooling to room temperature, the solvent is removed in vacuo to afford {2-[4-(4-Methoxy-phenyl)-butylamino]-ethyl}-carbamic acid tert-butyl ester as a viscous oil; [M+H]+ 323

Workup

  1. temperatureThe reaction mixture is heated
  2. temperatureat reflux for 2 hours
  3. customThe mixture is quenched by addition of MeOH
  4. temperatureheated to 70° C. for a further 2 hours
  5. temperatureAfter cooling to room temperature
  6. customthe solvent is removed in vacuo

Sources & evidence

ORD record
ord-6853e71b80434ff59be385da41af7933
Source dataset
uspto-grants-2014_04
Patent number
US08697687B2

Reaction notes

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