Benzaldehyde → HCID 69767185, compound

HRID 458759Notes

Reaction equation

HRID 458759 reaction equation
CO.[F:3][C:4]1([F:24])[CH2:8][CH2:7][C@@H:6]([C@@:9]([OH:23])([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:10]([O:12][CH2:13][CH2:14][CH2:15][NH2:16])=[O:11])[CH2:5]1.[CH:25](=O)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.[BH4-].[Na+]>C(OCC)(=O)C>[F:3][C:4]1([F:24])[CH2:8][CH2:7][C@@H:6]([C@@:9]([OH:23])([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:10]([O:12][CH2:13][CH2:14][CH2:15][NH:16][CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)=[O:11])[CH2:5]1

Participants

6

Reactant 4

HCID 240BenzaldehydeHCID 887MethanolHCID 4311764Sodium borohydrideHCID 69766803HCID 69766803, compound

Product 1

HCID 69767185HCID 69767185, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a methanol solution of 87 mg of 3-aminopropyl (2R)-2-((1R)-3,3-difluorocyclopentyl)-2-hydroxy-2-phenylethanoate, 35 mg of benzaldehyde was added at room temperature, stirred for 30 minutes at the same temperature, sodium borohydride was added, and further stirred for 30 minutes. The reaction liquid was diluted with ethyl acetate, washed successively with saturated aqueous sodium hydrogencarbonate solution and saturated brine, and dried over anhydrous sodium sulfate. Distilling the solvent off under reduced pressure, the resulting residue was purified on silica gel column chromatography (eluent: chloroform/methanol=50/1), to provide the title compound.

Workup

  1. additionwas added
  2. customThe reaction liquid
  3. washwashed successively with saturated aqueous sodium hydrogencarbonate solution and saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. distillationDistilling the solvent off under reduced pressure
  6. customthe resulting residue was purified on silica gel column chromatography (eluent: chloroform/methanol=50/1)

Sources & evidence

ORD record
ord-d34d39aaa4834feea5a8696838fa3041
Source dataset
uspto-grants-2007_03
Patent number
US07192969B2

Reaction notes

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