Methanol → HCID 18182182, compound

HRID 1359331Notes

Reaction equation

HRID 1359331 reaction equation
[BH4-].[Na+].[CH2:3]([C:10]1[C:15]([OH:16])=[CH:14][CH:13]=[C:12]([C:17]2([OH:24])[CH2:22][CH2:21][C:20](=[O:23])[CH2:19][CH2:18]2)[N:11]=1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.CO>CC(C)=O>[CH2:3]([C:10]1[C:15]([OH:16])=[CH:14][CH:13]=[C:12]([C:17]2([OH:24])[CH2:22][CH2:21][CH:20]([OH:23])[CH2:19][CH2:18]2)[N:11]=1)[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 4311764Sodium borohydrideHCID 18182324HCID 18182324, compound

Product 1

HCID 18182182HCID 18182182, compoundYield 54.3%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

67.4 mg of sodium borohydride was added to a mixture of 353 mg of 2-benzyl-3-hydroxy-6-(4-oxo-1-hydroxycyclohexyl)pyridine and 4 ml of methanol under ice-cooling, followed by stirring at the same temperature for one hour. Acetone was added thereto, and the solvent was removed. Then, the residue was subjected to silica gel column chromatography using 20% hexane/ethyl acetate, to give 193 mg of the target compound.

Workup

  1. temperaturecooling
  2. customthe solvent was removed

Sources & evidence

ORD record
ord-79c7da19b7764d46a4ef88482ad7b332
Source dataset
uspto-grants-2003_07
Patent number
US06599917B1

Reaction notes

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