tert-Butyl 4-oxopiperidine-1-carboxylate → 4-Butoxypiperidine

HRID 1281998Notes

Reaction equation

HRID 1281998 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][C:11](=[O:14])[CH2:10][CH2:9]1)=O)(C)(C)C.[H-].C([Al+]CC(C)C)C(C)C.O.O.O.O.[C:29]([CH:32]([CH:34]([C:36]([O-])=O)O)O)([O-])=O.[Na+].[K+]>C1COCC1.C1(C)C=CC=CC=1>[CH2:29]([O:14][CH:11]1[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]1)[CH2:32][CH2:34][CH3:36]

Participants

6

Reactant 3

HCID 735900tert-Butyl 4-oxopiperidine-1-carboxylateHCID 2724148Sodium potassium tartrate tetrahydrateHCID 21225700Diisobutylaluminumhydride

Product 1

HCID 224853894-Butoxypiperidine

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-20 °C

Procedure

To a solution of 10 g (50 mmol) of 1-t-butoxycarbonyl-4-piperidone (Aldrich) in 10 mL of THF at −78° C. was added 75 mL (75 mmol) of a 1 M solution of diisobutylaluminum hydride in toluene. The reaction mixture was allowed to warm to −20° C. and stirred for 3 h. After this time it was poured into 500 mL of sat'd solution of potassium sodium tartrate tetrahydrate (Rochelle salt), the mixture was stirred vigorously for 20 min, and the layers were separated. The aqueous layer was washed with ethyl acetate and the combined organic fractions were washed with brine, dried over MgSO4, filtered, and the filtrate was concentrated to give the title compound which was used without further purification.

Workup

  1. stirringthe mixture was stirred vigorously for 20 min
  2. customthe layers were separated
  3. washThe aqueous layer was washed with ethyl acetate
  4. washthe combined organic fractions were washed with brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-7e86c70c8efd44d5b493cde4ef41c298
Source dataset
uspto-grants-2002_09
Patent number
US06455548B2

Reaction notes

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