Sodium borohydride → 1-Benzyl-3,3-dimethylpiperidin-4-OL

HRID 396302Notes

Reaction equation

HRID 396302 reaction equation
[BH4-].[Na+].[CH2:3]([N:10]1[CH2:15][CH2:14][C:13](=[O:16])[C:12]([CH3:18])([CH3:17])[CH2:11]1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1>CO>[CH2:3]([N:10]1[CH2:15][CH2:14][CH:13]([OH:16])[C:12]([CH3:18])([CH3:17])[CH2:11]1)[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 97944131-Benzyl-3,3-dimethylpiperidin-4-one

Product 1

HCID 224957201-Benzyl-3,3-dimethylpiperidin-4-OL

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Sodium borohydride (0.456 g, 12.0 mmole) was added to the stirred solution of 1-benzyl-3,3-dimethylpiperidin-4-one [{prepared according to literature procedure described in U.S. Pat. No. 5,846,980} 5.4 g, 24.0 mmole] in methanol (25 ml) at 0-5° C. over a period of 15 min, and stirring was continued for 30 min. The reaction mixture was concentrated to dryness, triturated with water (25 ml) and extracted with ethyl acetate (2×100 ml). The extract was dried (sodium sulphate) and concentrated to dryness to furnish 1-benzyl-3,3-dimethyl-4-hydroxypiperidine as oil. Yield 5.2 g (96%), C14H2,NO, m/z 220 (M+1), PMR (CDCl3): 0.83 (3H, s, CH3), 1.13 (3H, s, CH3), 1.29 (1H, m, H5), 1.62-1.9 (2H, m, H2 & H5), 2.14 (1H, m, H6), 2.38 (1H, d, H2, j=12 Hz), 2.8 (1H, m, H6), 3.12 (1H, m, H4), 3.46 (2H, s, N—CH2), 7.3 (5H, m, ArH).

Workup

  1. customprepared
  2. concentrationThe reaction mixture was concentrated to dryness
  3. customtriturated with water (25 ml)
  4. extractionextracted with ethyl acetate (2×100 ml)
  5. dry with materialThe extract was dried (sodium sulphate)
  6. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-bd68eb6c4c484477a6f9c2f6ee059237
Source dataset
uspto-grants-2003_08
Patent number
US06608078B2

Reaction notes

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