Piperidin-4-ol → Tert-butyl 4-hydroxypiperidine-1-carboxylate

HRID 458748Notes

Reaction equation

HRID 458748 reaction equation
[OH:1][CH:2]1[CH2:7][CH2:6][NH:5][CH2:4][CH2:3]1.[C:8]([O:12][C:13](=O)[O:14]C(C)(C)C)([CH3:11])([CH3:10])[CH3:9]>C(Cl)(Cl)Cl.C(OCC)(=O)C>[OH:1][CH:2]1[CH2:7][CH2:6][N:5]([C:13]([O:12][C:8]([CH3:11])([CH3:10])[CH3:9])=[O:14])[CH2:4][CH2:3]1

Participants

5

Reactant 2

HCID 79341Piperidin-4-olHCID 10219638Carbonic acid, bis(1,1-dimethylethyl) ester

Product 1

HCID 643502Tert-butyl 4-hydroxypiperidine-1-carboxylateYield 90.5%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 10 g of 4-hydroxypiperidine in 300 ml of chloroform, 20 g of di-t-butylcarbonate was added under cooling with ice, followed by 2 hours' stirring at room temperature. The reaction liquid was diluted with ethyl acetate, washed successively with water and saturated brine, and dried over anhydrous sodium sulfate. Distilling the solvent off under reduced pressure, 18 g of the title compound was obtained.

Workup

  1. temperatureunder cooling with ice
  2. customThe reaction liquid
  3. washwashed successively with water and saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. distillationDistilling the solvent off under reduced pressure

Sources & evidence

ORD record
ord-85b0c20a3e05459281e0295933e8852f
Source dataset
uspto-grants-2007_03
Patent number
US07192969B2

Reaction notes

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