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

HRID 280982Notes

Reaction equation

HRID 280982 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.O1CCCC1.[BH4-].[Na+]>CO>[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 8028TetrahydrofuranHCID 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 887MethanolSolvent

Procedure

To a stirred mixture of ethyl 5-(1-benzyloxycarbonyl-4-piperidyl)valerate (26.8 g), tetrahydrofuran (200 ml) and sodium borohydride (13.4 g) is added dropwise methanol (40 ml) for 1.5 hours at 70°-80° C. After the addition is complete, the mixture is refluxed for 2 hours with stirring. After evaporation of solvent, the residue is diluted with water (300 ml) and extracted with ethyl acetate (300 ml). The extract is washed successively with 1N hydrochloric acid and water, dried over anhydrous magnesium sulfate and evaporated in vacuo to give 5-(1-benzyloxycarbonyl-4-piperidyl)pentanol (23 g) as a colorless oil.

Workup

  1. additionAfter the addition
  2. temperaturethe mixture is refluxed for 2 hours
  3. customAfter evaporation of solvent
  4. additionthe residue is diluted with water (300 ml)
  5. extractionextracted with ethyl acetate (300 ml)
  6. washThe extract is washed successively with 1N hydrochloric acid and water
  7. dry with materialdried over anhydrous magnesium sulfate
  8. customevaporated in vacuo

Sources & evidence

ORD record
ord-a479b85af5f34dffac85fa7442e5fddb
Source dataset
uspto-grants-1986_05
Patent number
US04591458

Reaction notes

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