Methanol → 5-(1-Benzyloxycarbonyl-4-piperidyl)pentanol

HRID 980612Notes

Reaction equation

HRID 980612 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][CH:14]([CH2:17][CH2:18][CH2:19][CH2:20][C:21](OCC)=[O:22])[CH2:13][CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[BH4-].[Na+].CO>O1CCCC1>[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][CH:14]([CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][OH:22])[CH2:13][CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 4311764Sodium borohydrideHCID 14046929Ethyl 5-(1-benzyloxycarbonyl-4-piperidyl)valerate

Product 1

HCID 140469305-(1-Benzyloxycarbonyl-4-piperidyl)pentanolYield 97.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In 200 ml of tetrahydrofuran is dissolved 26.8 g of ethyl 5-(1-benzyloxycarbonyl-4-piperidyl)valerate, and 13.4 g of sodium borohydride is added to the solution. Methanol (40 ml) is added dropwise to the mixture at 70° to 80° C. with stirring over the period of 1.5 hours, and after the addition is completed, refluxing is effected for another 2 hours. The reaction solution is concentrated under reduced pressure, and 300 ml of water is added to the residue, followed by extraction with 300 ml of ethyl acetate. The extract is washed with 50 ml of 1 N hydrochloric acid and 50 ml of water successively, dried over anhydrous magnesium sulfate and concentrated under reduced pressure to give 23 g of 5-(1-benzyloxycarbonyl-4-piperidyl)pentanol as a colorless oily material.

Workup

  1. additionis added to the solution
  2. additionafter the addition
  3. temperaturerefluxing
  4. waitis effected for another 2 hours
  5. concentrationThe reaction solution is concentrated under reduced pressure, and 300 ml of water
  6. additionis added to the residue
  7. extractionfollowed by extraction with 300 ml of ethyl acetate
  8. washThe extract is washed with 50 ml of 1 N hydrochloric acid and 50 ml of water successively
  9. dry with materialdried over anhydrous magnesium sulfate
  10. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-7a0603bcb3e94cdb90fea6f35a9529ae
Source dataset
uspto-grants-1987_01
Patent number
US04638000

Reaction notes

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