Sodium borohydride → HCID 69022176, compound

HRID 860798Notes

Reaction equation

HRID 860798 reaction equation
[BH4-].[Na+].[Cl:3][C:4]1[CH:29]=[CH:28][C:7]([C:8]([C:10]2[CH:11]=[CH:12][C:13]3[NH:19][C:18](=[O:20])[CH2:17][N:16]=[C:15]([C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=4)[C:14]=3[CH:27]=2)=[O:9])=[CH:6][CH:5]=1>CO>[Cl:3][C:4]1[CH:5]=[CH:6][C:7]([CH:8]([OH:9])[C:10]2[CH:11]=[CH:12][C:13]3[NH:19][C:18](=[O:20])[CH2:17][N:16]=[C:15]([C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=4)[C:14]=3[CH:27]=2)=[CH:28][CH:29]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 69020431HCID 69020431, compound

Product 1

HCID 69022176HCID 69022176, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Sodium tetrahydroborate (2.68 g) was added portionwise at 5° C. to a solution of intermediate (27) (0.0354 mol) in methanol (150 ml). The solution was poured into ice water and extracted with DCM. The organic layer was dried (MgSO4), filtered off and evaporated. The residue (12.27 g) was purified by column chromatography over silica gel (eluent: CH2Cl2/CH3OH/NH4OH 97/3/0.1). The pure fractions were collected and evaporated. The residue was crystallized from methanol, yielding 10.4 g (78%) of (±)-7-[(4-chlorophenyl)hydroxymethyl]-1,3-dihydro-5-phenyl-2H-1,4-benzodiazepin-2-one (intermediate 28).

Workup

  1. extractionextracted with DCM
  2. dry with materialThe organic layer was dried (MgSO4)
  3. filtrationfiltered off
  4. customevaporated
  5. customThe residue (12.27 g) was purified by column chromatography over silica gel (eluent: CH2Cl2/CH3OH/NH4OH 97/3/0.1)
  6. customThe pure fractions were collected
  7. customevaporated
  8. customThe residue was crystallized from methanol

Sources & evidence

ORD record
ord-d19833a944eb44d288e8040b286438c7
Source dataset
uspto-grants-2006_12
Patent number
US07153958B2

Reaction notes

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