Sodium borohydride → HCID 23003714, compound

HRID 396333Notes

Reaction equation

HRID 396333 reaction equation
[BH4-].[Na+].[CH2:3]([N:10]1[CH2:15][CH:14]([CH3:16])[C:13](=[O:17])[C:12]([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][CH:14]([CH3:16])[CH:13]([OH:17])[C:12]([CH3:18])([CH3:19])[CH2:11]1)[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 22278870HCID 22278870, compound

Product 1

HCID 23003714HCID 23003714, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Sodium borohydride (0.2 g, 5.26 mmole) was added to the stirred solution of 1-benzyl-3,3,5-trimethylpiperidin-4-one (2.0 g, 8.73 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-3,3,5-trimethylpiperidine as oil. Yield 1.9 g (91%), C15H23NO, m/z 234 (M+l).

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-e25741db05c644f985c1042b751ef8ea
Source dataset
uspto-grants-2003_08
Patent number
US06608078B2

Reaction notes

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