Sodium borohydride → (3S,4R)-1-Methyl-4-(2,4,6-trimethoxyphenyl)-3-piperidinol

HRID 1199355Notes

Reaction equation

HRID 1199355 reaction equation
[BH4-].[Na+].[CH3:3][N:4]1[CH2:9][CH2:8][CH:7]([C:10]2[C:15]([O:16][CH3:17])=[CH:14][C:13]([O:18][CH3:19])=[CH:12][C:11]=2[O:20][CH3:21])[C:6](=[O:22])[CH2:5]1>C(O)C.O>[OH:22][C@H:6]1[C@@H:7]([C:10]2[C:11]([O:20][CH3:21])=[CH:12][C:13]([O:18][CH3:19])=[CH:14][C:15]=2[O:16][CH3:17])[CH2:8][CH2:9][N:4]([CH3:3])[CH2:5]1

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 11780885HCID 11780885, compound

Product 1

HCID 11076869(3S,4R)-1-Methyl-4-(2,4,6-trimethoxyphenyl)-3-piperidinol

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

Sodium borohydride (10 g) is added with stirring to a solution, boiling under reflux, of 1-methyl-4-(2,4,6-trimethoxyphenyl)-piperidin-3-one in absolute ethanol. Stirring and heating under reflux is then continued for a further hour. On cooling, the reaction mixture is diluted with water, then concentrated in order to remove the ethanol and extracted with chloroform. The chloroform extract is washed with water, dried over anhydrous sodium sulfate and concentrated to give a solid residue which, on crystallization from acetone, gives the desired product (29.2 g) of melting point 124°-125° C.

Workup

  1. stirringStirring
  2. temperatureheating
  3. temperatureunder reflux
  4. waitis then continued for a further hour
  5. temperatureOn cooling
  6. concentrationconcentrated in order
  7. customto remove the ethanol
  8. extractionextracted with chloroform
  9. extractionThe chloroform extract
  10. washis washed with water
  11. dry with materialdried over anhydrous sodium sulfate
  12. concentrationconcentrated
  13. customto give a solid residue which
  14. customon crystallization from acetone

Sources & evidence

ORD record
ord-375cb3da2cca44e698e09761b10184c5
Source dataset
uspto-grants-1990_02
Patent number
US04900727

Reaction notes

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