Acetaldehyde → HCID 86597301, compound

HRID 1761156Notes

Reaction equation

HRID 1761156 reaction equation
[F:1][C:2]1([F:25])[CH2:6][CH2:5][C@@H:4]([C@@:7]([OH:24])([C:17]2[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][CH:18]=2)[C:8]([O:10][CH:11]2[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]2)=[O:9])[CH2:3]1.[CH:26](=O)[CH3:27].C([BH3-])#N.[Na+]>CO.C(Cl)(Cl)Cl>[F:25][C:2]1([F:1])[CH2:6][CH2:5][C@@H:4]([C@@:7]([OH:24])([C:17]2[CH:18]=[CH:19][C:20]([Cl:23])=[CH:21][CH:22]=2)[C:8]([O:10][CH:11]2[CH2:12][CH2:13][N:14]([CH2:26][CH3:27])[CH2:15][CH2:16]2)=[O:9])[CH2:3]1

Participants

6

Reactant 3

HCID 177AcetaldehydeHCID 5003444Sodium cyanoborohydrideHCID 69766274HCID 69766274, compound

Product 1

HCID 86597301HCID 86597301, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6212ChloroformSolvent

Procedure

To a solution of 25 mg of piperidin-4-yl(2R)-((1R)-3,3-difluorocyclopentyl)-2-hydroxy-2-(4-chlorophenyl)ethanoate in 1 ml of methanol, 50 mg of acetaldehyde and 10 mg of sodium cyanoborohydride were added at room temperature, followed by two hours' stirring at the same temperature. The reaction liquid was diluted with chloroform, washed successively with saturated sodium hydrogencarbonate solution and with saturated brine, and dried over anhydrous sodium sulfate. Distilling the solvent off under reduced pressure, the residue was purified on preparative thin layer chromatography (Kieselgel™60F254, Art5744 (Merck), chloroform/methanol=10/1) to provide the title compound.

Workup

  1. customThe reaction liquid
  2. washwashed successively with saturated sodium hydrogencarbonate solution and with saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. distillationDistilling the solvent off under reduced pressure
  5. customthe residue was purified on preparative thin layer chromatography (Kieselgel™60F254, Art5744 (Merck), chloroform/methanol=10/1)

Sources & evidence

ORD record
ord-df3dde2cc1214c7aa62c83d212e9b9cd
Source dataset
uspto-grants-2005_01
Patent number
US06846835B2

Reaction notes

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