Sodium borohydride → HCID 22405265, compound

HRID 441256Notes

Reaction equation

HRID 441256 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[CH:36]=[CH:35][CH:34]=[CH:33][C:9]=1[C:10]([NH:12][C:13]1[CH:32]=[CH:31][C:16]([C:17]([N:19]2[C:25]3[CH:26]=[CH:27][CH:28]=[CH:29][C:24]=3[C:23](=[O:30])[CH2:22][CH2:21][CH2:20]2)=[O:18])=[CH:15][CH:14]=1)=[O:11].[BH4-].[Na+]>CO.C(Cl)(Cl)Cl>[OH:30][CH:23]1[C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=2[N:19]([C:17](=[O:18])[C:16]2[CH:15]=[CH:14][C:13]([NH:12][C:10](=[O:11])[C:9]3[CH:33]=[CH:34][CH:35]=[CH:36][C:8]=3[C:3]3[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=3[CH3:1])=[CH:32][CH:31]=2)[CH2:20][CH2:21][CH2:22]1

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 22405232HCID 22405232, compound

Product 1

HCID 22405265HCID 22405265, compoundYield 93.2%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6212ChloroformSolvent

Procedure

To a solution of 1-{4-[2-(2-methylphenyl)benzoylamino]benzoyl}-2,3,4,5-tetrahydro-1H-1-benzazepin-5-one (620 mg) in methanol (20 ml) was added sodium borohydride (49.4 mg) and the mixture was stirred at ambient temperature for 4 hours. The mixture was diluted with chloroform and the solution was washed with water and brine, and dried over magnesium sulfate. The solvent was evaporated in vacuo to give a syrup and the residue was purified by silica gel column (30g, 1% methanol in chloroform) to give 5-hydroxy-1-{4-[2-(2-methylphenyl)benzoylamino]benzoyl}-2,3,4,5-tetrahydro-1H-1-benzazepine (580 mg).

Workup

  1. washthe solution was washed with water and brine
  2. dry with materialdried over magnesium sulfate
  3. customThe solvent was evaporated in vacuo
  4. customto give a syrup
  5. customthe residue was purified by silica gel column (30g, 1% methanol in chloroform)

Sources & evidence

ORD record
ord-a5a81026f3d64c4da1ee21ab9ffd8dee
Source dataset
uspto-grants-1996_05
Patent number
US05521170

Reaction notes

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