Sodium borohydride → HCID 70028630, compound

HRID 396320Notes

Reaction equation

HRID 396320 reaction equation
[BH4-].[Na+].[CH2:3]([N:10]1[CH2:15][CH2:14][C:13](=[O:16])[CH:12]([CH2:17][CH2:18][CH2:19][CH3:20])[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][CH2:18][CH2:19][CH3:20])[CH2:11]1)[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 68684462HCID 68684462, compound

Product 1

HCID 70028630HCID 70028630, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Sodium borohydride (0.4 g, 12.2 mmole) was added to the stirred solution of 1-benzyl-3-n-butylpiperidin-4-one (2.8 g, 9.3 mmole) in methanol (20 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-3-n-butyl-4-hydroxypiperidine as oil. Yield 2.5 g (86%), C16H25NO, m/z 248 (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-a64e2511cd1e436288b5d999e27e4f69
Source dataset
uspto-grants-2003_08
Patent number
US06608078B2

Reaction notes

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