Ammonium formate → (3RS)-3-amino-2,3-dihydro-5-isopropyl-1H-1,4-benzodiazepin-2-one

HRID 1596338Notes

Reaction equation

HRID 1596338 reaction equation
C(OC([NH:11][CH:12]1[N:18]=[C:17]([CH:19]([CH3:21])[CH3:20])[C:16]2[CH:22]=[CH:23][CH:24]=[CH:25][C:15]=2[NH:14][C:13]1=[O:26])=O)C1C=CC=CC=1.C([O-])=O.[NH4+]>CO.[Pd]>[NH2:11][CH:12]1[N:18]=[C:17]([CH:19]([CH3:21])[CH3:20])[C:16]2[CH:22]=[CH:23][CH:24]=[CH:25][C:15]=2[NH:14][C:13]1=[O:26]

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 135813678(3RS)-3-benzyloxycarbonylamino-2,3-dihydro-5-isopropyl-1H-1,4-benzodiazepin-2-one

Product 1

HCID 136041253(3RS)-3-amino-2,3-dihydro-5-isopropyl-1H-1,4-benzodiazepin-2-oneYield 85.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent2×

Procedure

To a suspension of Pd—C (5 wt %, 1.60 g) in methanol (60 ml) was added dropwise a solution of (3RS)-3-benzyloxycarbonylamino-2,3-dihydro-5-isopropyl-1H-1,4-benzodiazepin-2-one (8.00 g) in methanol (60 ml) and then ammonium formate (5.56 g) at room temperature. The reaction mixture was stirred at the same temperature for 1 hour. The catalyst was filtered on Celite®. The filtrate was concentrated in vacuo. The residue was taken up with ethyl acetate (100 ml) and saturated aqueous sodium hydrogen carbonate (100 ml). The organic layer was washed with a brine (100 ml). Dryness over sodium sulfate and evaporation gave (3RS)-3-amino-2,3-dihydro-5-isopropyl-1H-1,4-benzodiazepin-2-one (4.21 g). The product was used in a following reaction step without further purification.

Workup

  1. customat room temperature
  2. filtrationThe catalyst was filtered on Celite®
  3. concentrationThe filtrate was concentrated in vacuo
  4. washThe organic layer was washed with a brine (100 ml)
  5. customDryness over sodium sulfate and evaporation

Sources & evidence

ORD record
ord-1c93ff1faba8472c9c45e185cc71204a
Source dataset
uspto-grants-2001_09
Patent number
US06291452B1

Reaction notes

Loading…