Water → HCID 20542093, compound

HRID 2286171Notes

Reaction equation

HRID 2286171 reaction equation
[C:1]([C:4]1[CH:5]=[CH:6][C:7]2[N:13]([CH2:14][CH3:15])[C:12](=[O:16])[CH2:11][N:10]=[C:9]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=3[F:23])[C:8]=2[CH:24]=1)(=[O:3])[CH3:2].[BH4-].[Na+].O>CO>[CH2:14]([N:13]1[C:7]2[CH:6]=[CH:5][C:4]([CH:1]([OH:3])[CH3:2])=[CH:24][C:8]=2[C:9]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[F:23])=[N:10][CH2:11][C:12]1=[O:16])[CH3:15]

Participants

5

Reactant 3

HCID 962WaterHCID 4311764Sodium borohydrideHCID 20542077HCID 20542077, compound

Product 1

HCID 20542093HCID 20542093, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

12.7 g (39.2 mmol) of 7-acetyl-1-ethyl-5-(o-fluorophenyl)-1,3-dihydro-2H-1,4-benzodiazepin-2-one in 240 ml of methanol are treated in the cold while stirring with 743 mg (19.6 mmol) of sodium borohydride. The mixture is subsequently stirred at room temperature for 17 hours, treated with water and then with 2 N sulphuric acid and extracted with methylene chloride. The organic phase is washed with water, dried and evaporated. The residue is chromatographed on 500 g of silica gel using ethyl acetate/toluene (1:1) as the elution agent, and gives, from cyclohexane, 1-ethyl-5-(o-fluorophenyl)-1,3-dihydro-7-(1-hydroxyethyl)-2H-1,4-benzodiazepin-2-one of melting point 55°-57°.

Workup

  1. extractionwith 2 N sulphuric acid and extracted with methylene chloride
  2. washThe organic phase is washed with water
  3. customdried
  4. customevaporated
  5. customThe residue is chromatographed on 500 g of silica gel

Sources & evidence

ORD record
ord-14d0bce1649e4fa6a0f673b34d22fc00
Source dataset
uspto-grants-1982_04
Patent number
US04327026

Reaction notes

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