Sodium borohydride → HCID 13039296, compound

HRID 851065Notes

Reaction equation

HRID 851065 reaction equation
[CH:1]1([C:4]([N:6]2[CH2:11][CH2:10][C:9](=[O:12])[CH:8]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[CH2:7]2)=[O:5])[CH2:3][CH2:2]1.[BH4-].[Na+]>C(O)C>[CH:1]1([C:4]([N:6]2[CH2:11][CH2:10][C@@H:9]([OH:12])[C@H:8]([C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=3)[CH2:7]2)=[O:5])[CH2:2][CH2:3]1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 13039301HCID 13039301, compound

Product 1

HCID 13039296HCID 13039296, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

A solution of 4.77 g 1-cyclopropylcarbonyl-3-phenyl-4-piperidone in 50 ml of absolute ethanol is cooled to 4° C. and treated dropwise under nitrogen with a solution of 0.74 g of sodium borohydride in 50 ml of absolute ethanol over a 10 minute period, keeping the pot temperature below 10° C. After the addition is complete, the bath is removed. The mixture is cooled while diluting with 100 ml of saturated sodium chloride solution and, after stirring for a few minutes the ethanol is removed in vacuo and the aqueous residue is extracted with dichloromethane (1×150 ml, 2×100 ml). The combined dichloromethane extracts are washed with 150 ml of saturated sodium chloride solution, dried over anhydrous sodium sulfate, filtered and concentrated in vacuo to afford a yellow oil. The oil is chromatographed on 190 g of silica gel using ether as solvent followed by 5%, 10% and finally 50% acetone/ether mixture. The cis-isomer is eluted first followed by the trans-isomer as a colorless solid. Recrystallization from 5 ml of ethyl acetate affords product as a colorless crystalline solid, mp, 125°-127.5° C.

Workup

  1. customthe pot temperature below 10° C
  2. additionAfter the addition
  3. customthe bath is removed
  4. temperatureThe mixture is cooled
  5. additionwhile diluting with 100 ml of saturated sodium chloride solution
  6. customis removed in vacuo
  7. extractionthe aqueous residue is extracted with dichloromethane (1×150 ml, 2×100 ml)
  8. washThe combined dichloromethane extracts are washed with 150 ml of saturated sodium chloride solution
  9. dry with materialdried over anhydrous sodium sulfate
  10. filtrationfiltered
  11. concentrationconcentrated in vacuo
  12. customto afford a yellow oil
  13. customThe oil is chromatographed on 190 g of silica gel
  14. washThe cis-isomer is eluted first
  15. customRecrystallization from 5 ml of ethyl acetate
  16. customaffords product as a colorless crystalline solid, mp, 125°-127.5° C.

Sources & evidence

ORD record
ord-05f13f0945d74e69ad82e12dfce93666
Source dataset
uspto-grants-1983_05
Patent number
US04382141

Reaction notes

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