Sodium borohydride → 7-chloro-4,5-dihydro-3-[(E)-3-hydroxy-1-butenyl]-5-methyl-6H-imidazo[1,5-a][1,4]benzodiazepin-6-one

HRID 1606999Notes

Reaction equation

HRID 1606999 reaction equation
[Cl:1][C:2]1[C:7]2[C:8](=[O:22])[N:9]([CH3:21])[CH2:10][C:11]3[N:12]([CH:13]=[N:14][C:15]=3/[CH:16]=[CH:17]/[C:18](=[O:20])[CH3:19])[C:6]=2[CH:5]=[CH:4][CH:3]=1.[BH4-].[Na+]>CN(C)C=O.C(O)C>[Cl:1][C:2]1[C:7]2[C:8](=[O:22])[N:9]([CH3:21])[CH2:10][C:11]3[N:12]([CH:13]=[N:14][C:15]=3/[CH:16]=[CH:17]/[CH:18]([OH:20])[CH3:19])[C:6]=2[CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 4311764Sodium borohydride2×HCID 198515567-chloro-4,5-dihydro-3-[(E)-3-oxo-1-butenyl]-5-methyl-6H-imidazo[1,5-a][1,4]benzodiazepin-6-one

Product 1

HCID 198515897-chloro-4,5-dihydro-3-[(E)-3-hydroxy-1-butenyl]-5-methyl-6H-imidazo[1,5-a][1,4]benzodiazepin-6-one

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6228DimethylformamideSolvent

Procedure

2.4 g (7.6 mmol) of 7-chloro-4,5-dihydro-3-[(E)-3-oxo-1-butenyl]-5-methyl-6H-imidazo[1,5-a][1,4]benzodiazepin-6-one was dissolved in 50 ml of dimethylformamide while warming. Thereafter, the solution was diluted with 280 ml of ethanol. 0.6 g (15.8 mmol) of sodium borohydride was added to this solution and the mixture was stirred at 20° for 2.5 hours. Thereafter, a further 0.2 g of sodium borohydride was added thereto. After a total reaction period of 4.5 hours the mixture was evaporated in a vacuum. The residue, which still contained dimethylformamide, was poured on to ice/water and stirred at 0° for 1 hour. The crystallizate was filtered off under suction and dried. There was obtained 7-chloro-4,5-dihydro-3-[(E)-3-hydroxy-1-butenyl]-5-methyl-6H-imidazo[1,5-a][1,4]benzodiazepin-6-one as white crystals of melting point 232°-233°.

Workup

  1. temperaturewhile warming
  2. customAfter a total reaction period of 4.5 hours the mixture
  3. customwas evaporated in a vacuum
  4. additionThe residue, which still contained dimethylformamide, was poured on to ice/water
  5. stirringstirred at 0° for 1 hour
  6. filtrationThe crystallizate was filtered off under suction
  7. customdried

Sources & evidence

ORD record
ord-5d5b470cfe2a40bb86a3a2b68c36848f
Source dataset
uspto-grants-1989_09
Patent number
US04863920

Reaction notes

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