Sodium borohydride → 1,3-Dibenzyl-4-hydroxypiperidine

HRID 396327Notes

Reaction equation

HRID 396327 reaction equation
[BH4-].[Na+].[CH2:3]([N:10]1[CH2:15][CH2:14][C:13](=[O:16])[CH:12]([CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[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]([CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH2:11]1)[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 230036591,3-Dibenzylpiperidin-4-one

Product 1

HCID 230037131,3-Dibenzyl-4-hydroxypiperidine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Sodium borohydride (0.3 g, 9.0 mmole) was added to the stirred solution of 1,3-dibenzylpiperidin-4-one (1.8 g, 6.45 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 1,3-dibenzyl-4-hydroxypiperidine as oil. Yield 1.7 g (91%), C19H23NO, m/z 282 (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-d8251a4e3047489486d9c6755c186134
Source dataset
uspto-grants-2003_08
Patent number
US06608078B2

Reaction notes

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