Sodium borohydride → 3-Azido-3-(6-(trifluoromethyl)pyridin-3-yl)propan-1-ol

HRID 657743Notes

Reaction equation

HRID 657743 reaction equation
[N:1]([CH:4]([C:8]1[CH:9]=[N:10][C:11]([C:14]([F:17])([F:16])[F:15])=[CH:12][CH:13]=1)[CH2:5][CH:6]=[O:7])=[N+:2]=[N-:3].[BH4-].[Na+]>O1CCCC1.[Cl-].[Na+].O>[N:1]([CH:4]([C:8]1[CH:9]=[N:10][C:11]([C:14]([F:15])([F:16])[F:17])=[CH:12][CH:13]=1)[CH2:5][CH2:6][OH:7])=[N+:2]=[N-:3]

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 581035833-Azido-3-(6-(trifluoromethyl)pyridin-3-yl)propanal

Product 1

HCID 581035943-Azido-3-(6-(trifluoromethyl)pyridin-3-yl)propan-1-ol

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

To a stirred solution of the crude 3-azido-3-(6-(trifluoromethyl)pyridin-3-yl)propanal (5.0 g, 20.5 mmol) in tetrahydrofuran (100 mL) at 0° C. was added sodium tetrahydroborate (1.52 g, 40.1 mmol). The mixture was stirred at room temperature for 10 minutes. After completion of the reaction, brine was added and the mixture was extracted with ether. The organic layer was dried and concentrated to afford a crude oil which was purified by silica gel chromatography to afford a light yellow oil.

Workup

  1. additionwas added
  2. extractionthe mixture was extracted with ether
  3. customThe organic layer was dried
  4. concentrationconcentrated
  5. customto afford a crude oil which
  6. customwas purified by silica gel chromatography
  7. customto afford a light yellow oil

Sources & evidence

ORD record
ord-87cb1a78999944e1ac721c3b941c7331
Source dataset
uspto-grants-2011_12
Patent number
US08076345B2

Reaction notes

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