Sodium borohydride → (5-Bromo-2-(2-methylpiperidin-1-YL)phenyl)methanol

HRID 219871

Reaction equation

HRID 219871 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([N:10]2[CH2:15][CH2:14][CH2:13][CH2:12][CH:11]2[CH3:16])=[C:6]([CH:9]=1)[CH:7]=[O:8].[BH4-].[Na+]>CO.[NH4+].[Cl-]>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([N:10]2[CH2:15][CH2:14][CH2:13][CH2:12][CH:11]2[CH3:16])=[C:6]([CH2:7][OH:8])[CH:9]=1

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 230911015-Bromo-2-(2-methylpiperidin-1-YL)benzaldehyde

Product 1

HCID 58554197(5-Bromo-2-(2-methylpiperidin-1-YL)phenyl)methanolYield 97%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 25517Ammonium ChlorideSolvent

Procedure

To a solution of 5-bromo-2-(2-methylpiperidin-1-yl)benzaldehyde (16.30 g; 57.76 mmol) in MeOH (300 mL) was added sodium borohydride (2.19 g; 57.76 mmol) at 5° C. in a portion-wise fashion and stirred for 30 min. After this time, reaction mixture was diluted with a saturated aqueous solution of NH4Cl (300 mL), extracted with EtOAc. The org layers were washed with aqueous solution of NH4Cl (150 mL), brine (300 mL), dried over MgSO4 and evaporated under vacuum to give the title compound as a yellow oil (15.9 g, 97%). LC/MS (Method A): 285.6 (M+H)+. HPLC (Method A): Rt 2.13 min (Purity: 94.9%).

Workup

  1. customAfter this time, reaction mixture
  2. extractionextracted with EtOAc
  3. washThe org layers were washed with aqueous solution of NH4Cl (150 mL), brine (300 mL)
  4. dry with materialdried over MgSO4
  5. customevaporated under vacuum

Sources & evidence

ORD record
ord-7623db50dd62442a9174e143c5e24cd4
Source dataset
uspto-grants-2012_06
Patent number
US08202865B2

Linked notes

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