Ammonia → 3(R)-t-Butoxycarbonylamino-2,3,4,5-tetrahydro-1-[[2'-aminomethyl[1,1'-biphenyl]-4-yl]methyl]-1H-benzazepin-2-one

HRID 1740259Notes

Reaction equation

HRID 1740259 reaction equation
[C:1]([O:5][C:6]([NH:8][C@@H:9]1[CH2:15][CH2:14][C:13]2[CH:16]=[CH:17][CH:18]=[CH:19][C:12]=2[N:11]([CH2:20][C:21]2[CH:26]=[CH:25][C:24]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=3[C:33]#[N:34])=[CH:23][CH:22]=2)[C:10]1=[O:35])=[O:7])([CH3:4])([CH3:3])[CH3:2].N>C(O)C.[Ni]>[C:1]([O:5][C:6]([NH:8][C@@H:9]1[CH2:15][CH2:14][C:13]2[CH:16]=[CH:17][CH:18]=[CH:19][C:12]=2[N:11]([CH2:20][C:21]2[CH:22]=[CH:23][C:24]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=3[CH2:33][NH2:34])=[CH:25][CH:26]=2)[C:10]1=[O:35])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 222AmmoniaHCID 228774623(R)-t-Butoxycarbonylamino-2,3,4,5-tetrahydro-1-[[2'-cyano[1,1'-biphenyl]-4-yl]methyl]-1H-benzazepin-2-one

Product 1

HCID 228774603(R)-t-Butoxycarbonylamino-2,3,4,5-tetrahydro-1-[[2'-aminomethyl[1,1'-biphenyl]-4-yl]methyl]-1H-benzazepin-2-oneYield 74.4%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

To a solution of 200 mg (0.43 mmol) of the intermediate obtained in Step B in 5 mL of ethanol was added 5 mL of liquid ammonia and the resulting mixture hydrogenated at 200-400 psi and 80° C. for 6 hours over 60 mg of Raney nickel. The reaction mixture was cautiously vented and all volatiles removed by a steady stream of nitrogen. The residue was redissolved in chloroform, filtered through Celite and the filtrate concentrated under vacuum to give 149 mg (0.32 mmol, 74%) of the product as a white foam which was used without purification.

Workup

  1. customall volatiles removed by a steady stream of nitrogen
  2. dissolutionThe residue was redissolved in chloroform
  3. filtrationfiltered through Celite
  4. concentrationthe filtrate concentrated under vacuum

Sources & evidence

ORD record
ord-02265ec61e454480ab78ae580debf261
Source dataset
uspto-grants-1999_10
Patent number
US05968924

Reaction notes

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