Sodium borohydride → 2-((3-Bromobenzyl)(methyl)amino)-1-p-tolylethanol

HRID 576092

Reaction equation

HRID 576092 reaction equation
[BH4-].[Na+].[Br:3][C:4]1[CH:5]=[C:6]([CH:20]=[CH:21][CH:22]=1)[CH2:7][N:8]([CH3:19])[CH2:9][C:10]([C:12]1[CH:17]=[CH:16][C:15]([CH3:18])=[CH:14][CH:13]=1)=[O:11]>CO>[Br:3][C:4]1[CH:5]=[C:6]([CH:20]=[CH:21][CH:22]=1)[CH2:7][N:8]([CH3:19])[CH2:9][CH:10]([C:12]1[CH:13]=[CH:14][C:15]([CH3:18])=[CH:16][CH:17]=1)[OH:11]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 620376912-((3-Bromobenzyl)(methyl)amino)-1-p-tolylethanone

Product 1

HCID 667881872-((3-Bromobenzyl)(methyl)amino)-1-p-tolylethanolYield 93%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Sodium borohydride (646 mg, 17.1 mmol) was added over a period of 10 minutes to an ice-cooled solution of the product from Step A (4.89 g, 15.0 mmol) in methanol (85 mL). The reaction mixture was allowed to warm to room temperature and continued to stir for an additional 2 hours. The solvent was removed under reduced pressure and the residue was diluted with water and extracted with methylene chloride (3×). The combined extracts were dried over sodium sulfate, filtered, and concentrated in vacuo to provide 2-((3-bromobenzyl)(methyl)amino)-1-p-tolylethanol (4.58 g, 93%) as an orange oil: 1H NMR (300 MHz, CDCl3) δ 7.45 (s, 1H), 7.40 (d, J=5.8 Hz, 1H), 7.25-7.13 (m, 6H), 4.72 (dd, J=10.0, 3.7 Hz, 1H), 3.86 (br s, 1H), 3.68 (d, J=13.4 Hz, 1H), 3.49 (d, J=13.2 Hz, 1H), 2.62-2.47 (m, 2H), 2.33 (s, 3H), 2.30 (s, 3H).

Workup

  1. customThe solvent was removed under reduced pressure
  2. additionthe residue was diluted with water
  3. extractionextracted with methylene chloride (3×)
  4. dry with materialThe combined extracts were dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-de637d5168d24e59ba948c1c0cfac2d4
Source dataset
uspto-grants-2015_05
Patent number
US09034899B2

Linked notes

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