Sodium borohydride → HCID 178519503, compound

HRID 2383378Notes

Reaction equation

HRID 2383378 reaction equation
[CH:1]1([C:7]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)([C:9]2[N:13](CN3CCCC3)[N:12]=[CH:11][N:10]=2)[OH:8])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[BH4-].[Na+]>C(O)C>[CH:20]1([C:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)([C:9]2[N:10]=[CH:11][NH:12][N:13]=2)[OH:8])[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25]1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 59145963Cyclohexyl(phenyl)[1-(pyrrolidin-1-ylmethyl)-1H-1,2,4-triazol-5-yl]methanol

Product 1

HCID 178519503HCID 178519503, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Cyclohexyl(phenyl)[1-(pyrrolidin-1-ylmethyl)-1H-1,2,4-triazol-5-yl]methanol (Preparation 17, 27.28 g, 80.12 mmol) was dissolved in ethanol (400 ml) and sodium borohydride (3.03 g, 80.1 mmol) added portionwise. After stirring at reflux for 3 hours the reaction was left to cool to room temperature over 18 hrs. The solvent was removed in vacuo and the residue purified by column chromatography on silica gel eluting with pentane:ethyl acetate (3:1 to 0:1, by volume) to furnish the title compound as a white foam, in 79% yield, 16.4 g.

Workup

  1. temperatureat reflux for 3 hours the reaction
  2. waitwas left
  3. customThe solvent was removed in vacuo
  4. customthe residue purified by column chromatography on silica gel eluting with pentane:ethyl acetate (3:1 to 0:1, by volume)

Sources & evidence

ORD record
ord-d55b26dcfb8c42a5859f27c61146c650
Source dataset
uspto-grants-2012_09
Patent number
US08263623B2

Reaction notes

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