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

HRID 864500Notes

Reaction equation

HRID 864500 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(OCC)(=O)C.CCCCCC>O1CCCC1>[C:8]([O:12][C:13]([N:5]1[CH2:6][CH2:7][CH:2]([OH:1])[CH2:3][CH2:4]1)=[O:14])([CH3:11])([CH3:10])[CH3:9]

Participants

5

Reactant 3

HCID 79341Piperidin-4-olHCID 10219638Carbonic acid, bis(1,1-dimethylethyl) esterHCID 21226206Ethyl acetate hexane

Product 1

HCID 643502Tert-butyl 4-hydroxypiperidine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 4-hydroxypiperidine (5.05 g; 0.05 mole) in 100 ml of tetrahydrofuran was stirred and cooled in an ice-water bath. Di-tert.butylcarbonate (10.9 g; 0.05 mole) was added and stirring was continued at room temperature for 3 hrs. The solvent was removed under reduced pressure. An oily residue was triturated with petroleum ether. Recrystallization from petroleum ether yielded 9.21 g (92%). Rf (silica gel)=0.42 (ethyl acetate/n-hexane 1:

Workup

  1. temperaturecooled in an ice-water bath
  2. customThe solvent was removed under reduced pressure
  3. customAn oily residue was triturated with petroleum ether
  4. customRecrystallization from petroleum ether
  5. customyielded 9.21 g (92%)

Sources & evidence

ORD record
ord-73b71a0403004fe081208b97d2703e38
Source dataset
uspto-grants-1996_10
Patent number
US05563158

Reaction notes

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