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

HRID 2410489Notes

Reaction equation

HRID 2410489 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[CH2:16][CH3:17])=[C:6]([CH:9]=1)[CH:7]=[O:8].[BH4-].[Na+]>CO>[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[CH2:16][CH3:17])=[C:6]([CH2:7][OH:8])[CH:9]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 585541245-Bromo-2-(2-ethylpiperidin-1-YL)benzaldehyde

Product 1

HCID 58554150(5-Bromo-2-(2-ethylpiperidin-1-YL)phenyl)methanolYield 88%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 5-bromo-2-(2-ethylpiperidin-1-yl)benzaldehyde (10 g, 48.4 mmol) in methanol (100 mL) under nitrogen was added sodium borohydride (1.28 g, 48.4 mmol) at 0° C. in portions. The reaction mixture was stirred at RT for 1 hour, then evaporated to remove methanol. The resulting crude was taken up with water (100 mL) and extracted with EtOAc. The organic layer was washed with water, then dried (Na2SO4) and concentrated under reduced pressure to afford the title compound as a yellow oil (8.8 g, 88%). 1H NMR (DMSO-d6, 400 MHz) δ 7.55 (1H, s), 7.34-7.54 (1H, m), 7.08 (1H, d), 5.19 (1H, t), 4.62 (1H, d), 4.46 (1H, d), 2.77-2.84 (2H, m), 2.45 (1H, m), 1.74 (2H, t), 1.55 (2H, t), 1.33 (2H, m), 1.17 (2H, m), 0.62 (3H, t).

Workup

  1. customevaporated
  2. customto remove methanol
  3. extractionextracted with EtOAc
  4. washThe organic layer was washed with water
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-6e50c73893d44d81b94b7c5f66d4c036
Source dataset
uspto-grants-2014_08
Patent number
US08815919B2

Reaction notes

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