Diboron → HCID 20452655, compound

HRID 1462372Notes

Reaction equation

HRID 1462372 reaction equation
B#B.[CH2:3]([NH:10][C:11](=O)[CH2:12][CH2:13][C:14]1[CH:19]=[CH:18][C:17]([O:20][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[C:16]([C:28]([O:30][CH3:31])=[O:29])[CH:15]=1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1>O1CCCC1>[CH2:21]([O:20][C:17]1[CH:18]=[CH:19][C:14]([CH2:13][CH2:12][CH2:11][NH:10][CH2:3][C:4]2[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=2)=[CH:15][C:16]=1[C:28]([O:30][CH3:31])=[O:29])[C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1

Participants

4

Reactant 2

HCID 6328200DiboronHCID 54114698HCID 54114698, compound

Product 1

HCID 20452655HCID 20452655, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Selective reduction of the amide group in 3-(4-benzyloxy-3-methoxycarbonyl-phenyl)-propionic acid N-benzylamide using diborane in tetrahydrofuran for a reaction time of 48 hours at a temperature of 20°-25° yields N-[3-(4-benzyloxy-3-methoxycarbonyl-phenyl)-propyl]benzylamine, which, in the form of the crude product, is converted by means of hydrogen in the presence of palladium-on-charcoal catalyst (50%), in methanol as the solvent, at a temperature of 15°-20° to N-[3-(4-hydroxy-3-methoxycarbonylphenyl)-propyl]-benzylamine with a melting point of 75°-77° (from isopropanol).

Workup

  1. customfor a reaction time of 48 hours
  2. customat a temperature of 20°-25°

Sources & evidence

ORD record
ord-22e261fdf78b4a3fba04b407fae0f983
Source dataset
uspto-grants-1984_07
Patent number
US04460580

Reaction notes

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