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

HRID 400761Notes

Reaction equation

HRID 400761 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 (obtained in step 1, 10 g, 0.0484 mol) in methanol (100 mL) under nitrogen, was added sodium borohydride (1.28 g, 0.0484 mol) at 0° C. in portions. After being stirred at room temperature for a period of 1 h, the reaction mixture was evaporated to remove methanol. The resulting crude product was taken in water (100 mL) and extracted in ethyl acetate. The separated organic layer was washed with water, dried over sodium sulphate and concentrated under reduced pressure to afford the titled compound as yellow liquid (8.8 g, 88%). 1H NMR (DMSO-d6, 400 MHz) δ 7.54-7.55 (1H, s), 7.34-7.54 (1H, m), 7.07-7.09 (1H, d), 5.17-5.20 (1H, t), 4.59-4.64 (1H, d), 4.43-4.48 (1H, d), 2.77-2.84 (2H, m), 2.442-2.449 (1H, m), 1.74 (2H, t), 1.53-1.56 (2H, t), 1.32-1.34 (2H, m), 1.15-1.19 (2H, m), 0.60-0.64 (3H, t).

Workup

  1. customthe reaction mixture was evaporated
  2. customto remove methanol
  3. extractionextracted in ethyl acetate
  4. washThe separated organic layer was washed with water
  5. dry with materialdried over sodium sulphate
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-7e5f0b27111e44cfa6ea2065cdea3bd2
Source dataset
uspto-grants-2014_06
Patent number
US08741923B2

Reaction notes

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