Sodium borohydride → 1-[6-(4-Benzotriazol-2-yl-but-1-ynyl)-pyridin-2-yl]-ethanol

HRID 422427Notes

Reaction equation

HRID 422427 reaction equation
[BH4-].[Na+].[N:3]1[N:4]([CH2:12][CH2:13][C:14]#[C:15][C:16]2[N:21]=[C:20]([C:22](=[O:24])[CH3:23])[CH:19]=[CH:18][CH:17]=2)[N:5]=[C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=12>CO>[N:3]1[N:4]([CH2:12][CH2:13][C:14]#[C:15][C:16]2[N:21]=[C:20]([CH:22]([OH:24])[CH3:23])[CH:19]=[CH:18][CH:17]=2)[N:5]=[C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=12

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 66598247HCID 66598247, compound

Product 1

HCID 665982351-[6-(4-Benzotriazol-2-yl-but-1-ynyl)-pyridin-2-yl]-ethanolYield 53%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

NaBH4 (99 mg, 1.6 mmol) was added to a solution of 1-[6-(4-benzotriazol-2-yl-but-1-ynyl)-pyridin-2-yl]-ethanone (380 mg, 1.31 mmol) in MeOH (5 mL) at 0° C. The reaction mixture was stirred at room temperature for 30 min, quenched by the addition of water at 0° C. and extracted twice with DCM. The organic phase was washed with water, dried over Na2SO4, filtered and evaporated. The crude residue was purified by flash chromatography (cyclohexane/AcOEt 3:2) to yield 202 mg (0.69 mmol, 53%) of 1-[6-(4-benzotriazol-2-yl-but-1-ynyl)-pyridin-2-yl]-ethanol as a colorless oil.

Workup

  1. customquenched by the addition of water at 0° C.
  2. extractionextracted twice with DCM
  3. washThe organic phase was washed with water
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. customevaporated
  7. customThe crude residue was purified by flash chromatography (cyclohexane/AcOEt 3:2)

Sources & evidence

ORD record
ord-f7244a79f82e45b3b99fb61382003c8d
Source dataset
uspto-grants-2012_01
Patent number
US08101637B2

Reaction notes

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