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

HRID 1058843Notes

Reaction equation

HRID 1058843 reaction equation
[NH:1]1[CH2:6][CH2:5][CH:4]([OH:7])[CH2:3][CH2:2]1.[C:8]([O:12][C:13](=O)[O:14]C(C)(C)C)([CH3:11])([CH3:10])[CH3:9]>O1CCCC1>[C:8]([O:12][C:13]([N:1]1[CH2:6][CH2:5][CH:4]([OH:7])[CH2:3][CH2:2]1)=[O:14])([CH3:11])([CH3:10])[CH3:9]

Participants

4

Reactant 2

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

Product 1

HCID 643502Tert-butyl 4-hydroxypiperidine-1-carboxylateYield 91%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 25 g (247 mmol) 4-piperidinol in 350 mL dry tetrahydrofuran (THF) at 0° C. was added dropwise 60.2 g (276 mmol) di-t-butylcarbonate in 350 mL dry THF. The reaction was allowed to warm to room temperature (rt) and stirred overnight. The solvent was removed under reduced pressure, the resulting residue dissolved in 700 mL CH2Cl2 and the solution extracted with H2O (1×400 mL), dried over MgSO4, filtered and rotary evaporated to yield 45 g (91%) of N-(t-butoxycarbonyl)-4-piperidinol as an oil which slowly solidified to white crystals. 1H NMR (CDCl3) δ 3.75-3.96 (m, 3H); 2.92-3.13 (m, 2H); 1.80-1.93 (m, 4H); and 1.48 (s, 9H).

Workup

  1. customThe solvent was removed under reduced pressure
  2. dissolutionthe resulting residue dissolved in 700 mL CH2Cl2
  3. extractionthe solution extracted with H2O (1×400 mL)
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customrotary evaporated

Sources & evidence

ORD record
ord-1b71284b192346958af13cb54ae90fb7
Source dataset
uspto-grants-2003_02
Patent number
US06518285B2

Reaction notes

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