Sodium borohydride → HCID 67606120, compound

HRID 362780Notes

Reaction equation

HRID 362780 reaction equation
[BH4-].[Na+].[CH3:3][O:4][CH:5]1[C:10](=[O:11])[CH2:9][CH2:8][N:7]([CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH2:6]1>C(O)C>[CH3:3][O:4][C@H:5]1[C@H:10]([OH:11])[CH2:9][CH2:8][N:7]([CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH2:6]1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 15078438HCID 15078438, compound

Product 1

HCID 67606120HCID 67606120, compoundYield 25.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Sodium borohydride (7.7 g) was added portionwise to a stirred solution of 3-methoxy-1-(phenylmethyl)-4-piperidinone (44.8 g) in ethanol (610 ml). Upon completion, the whole was cooled to room temperature and stirring was continued for 3 hours at room temperature. The reaction mixture was concentrated to a volume of about 150 ml. Water (300 ml) was added to the concentrate and all traces of ethanol were evaporated. After cooling, the mixture was extracted with diethylether. The extract was washed with water, dried, filtered and evaporated. The oily residue was purified by column-chromatography over silica gel (eluent: CHCl3 /CH3OH 96/4). The pure fractions were collected and the eluent was evaporated. The residue was separated by column-chromatography over silica gel (eluent: hexane/CHCl3 /(CH3OH/NH3) 50/50/1). The first fraction was collected and the eluent evaporated, yielding 11.5 g (25.5%) of trans-3-methoxy-1-(phenylmethyl)-4-piperidinol (intermediate 1). The second fraction was collected and the eluent evaporated, yielding 7.7 g (17.1%) of cis-3-methoxy-1-(phenylmethyl)-4-piperidinol (intermediate 2).

Workup

  1. concentrationThe reaction mixture was concentrated to a volume of about 150 ml
  2. additionWater (300 ml) was added to the
  3. concentrationconcentrate
  4. customall traces of ethanol were evaporated
  5. temperatureAfter cooling
  6. extractionthe mixture was extracted with diethylether
  7. washThe extract was washed with water
  8. customdried
  9. filtrationfiltered
  10. customevaporated
  11. customThe oily residue was purified by column-chromatography over silica gel (eluent: CHCl3 /CH3OH 96/4)
  12. customThe pure fractions were collected
  13. customthe eluent was evaporated
  14. customThe residue was separated by column-chromatography over silica gel (eluent: hexane/CHCl3 /(CH3OH/NH3) 50/50/1)
  15. customThe first fraction was collected
  16. customthe eluent evaporated

Sources & evidence

ORD record
ord-c4bb07d7c26348ada74ffb3b50064462
Source dataset
uspto-grants-1999_02
Patent number
US05872131

Reaction notes

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