Sodium Hydroxide → HCID 69426324, compound

HRID 1592332Notes

Reaction equation

HRID 1592332 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([CH3:13])([CH3:12])[CH2:10][NH2:11])=[CH:4][CH:3]=1.[CH2:14]([O:21][C:22](=[O:32])[NH:23][CH:24]1[CH2:29][CH2:28][CH2:27][CH2:26][CH:25]1[CH:30]=O)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.[BH4-].[Na+].[OH-].[Na+]>CO>[CH2:14]([O:21][C:22](=[O:32])[NH:23][CH:24]1[CH2:29][CH2:28][CH2:27][CH2:26][CH:25]1[CH2:30][NH:11][CH2:10][C:9]([CH3:13])([CH3:12])[CH2:8][C:5]1[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

6

Reactant 4

HCID 14798Sodium HydroxideHCID 4311764Sodium borohydrideHCID 22259004HCID 22259004, compoundHCID 62740631HCID 62740631, compound

Product 1

HCID 69426324HCID 69426324, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

3-(4-Fluorophenyl)-2,2-dimethylpropylamine (253 mg, 1.39 mmol) and (2-formylcyclohexyl)carbamic acid benzyl ester (363 mg, 1.39 mmol) were dissolved in methanol (6 mL) and stirred at room temperature for 4 h. Sodium borohydride (84 mg, 2.22 mmol) was added, and the mixture was stirred for 30 min. 1.0 M aqueous sodium hydroxide was added, and the mixture was extracted with ether. The organic phase was washed with saturated aqueous sodium chloride and dried over sodium sulfate, and concentrated under vacuum. The residue was purified by flash column chromatography on silica gel, eluting with 5% methanol in dichloromethane containing 0.5% aqueous ammonium hydroxide, to provide a colorless gum (450 mg, 76%).

Workup

  1. stirringthe mixture was stirred for 30 min
  2. extractionthe mixture was extracted with ether
  3. washThe organic phase was washed with saturated aqueous sodium chloride
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated under vacuum
  6. customThe residue was purified by flash column chromatography on silica gel
  7. washeluting with 5% methanol in dichloromethane containing 0.5% aqueous ammonium hydroxide

Sources & evidence

ORD record
ord-49eab2514ae64f91b61d21c4714ef338
Source dataset
uspto-grants-2007_11
Patent number
US07291744B2

Reaction notes

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