Sodium borohydride → 1-Benzyl-4-hydroxy-3-isopropylpiperidine

HRID 396318Notes

Reaction equation

HRID 396318 reaction equation
[BH4-].[Na+].[CH2:3]([N:10]1[CH2:15][CH2:14][C:13](=[O:16])[CH:12]([CH:17]([CH3:19])[CH3:18])[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])[CH:12]([CH:17]([CH3:19])[CH3:18])[CH2:11]1)[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 23003699HCID 23003699, compound

Product 1

HCID 230037111-Benzyl-4-hydroxy-3-isopropylpiperidine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Sodium borohydride (0.5 g, 15.6 mmole) was added to the stirred solution of 1-benzyl-3-isopropylpiperid-4-one (3.3 g, 14.2 mmole) in methanol (25 ml) at 0-5° C. over a period of 5 min, and stirring was continued for 1 hr at ambient temperature. The reaction mixture was concentrated to dryness, triturated with water (20 ml) and extracted with ethyl acetate. The ethyl acetate extract was dried (Na2SO4) and concentrated to dryness to furnish 1-benzyl-4-hydroxy-3-isopropylpiperidine as oil. Yield 2.9 g (85%), C15H23NO, m/z 234 (M+1).

Workup

  1. concentrationThe reaction mixture was concentrated to dryness
  2. customtriturated with water (20 ml)
  3. extractionextracted with ethyl acetate
  4. extractionThe ethyl acetate extract
  5. dry with materialwas dried (Na2SO4)
  6. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-6333fe5c6c9942e694edddd51596d8da
Source dataset
uspto-grants-2003_08
Patent number
US06608078B2

Reaction notes

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