Triethylamine → 1-Boc-3-hydroxypiperidine

HRID 1058848Notes

Reaction equation

HRID 1058848 reaction equation
[OH:1][CH:2]1[CH2:7][CH2:6][CH2:5][NH:4][CH2:3]1.CCN(CC)CC.[C:15]([O:19][C:20](=O)[O:21]C(C)(C)C)([CH3:18])([CH3:17])[CH3:16]>C1COCC1>[C:15]([O:19][C:20]([N:4]1[CH2:5][CH2:6][CH2:7][CH:2]([OH:1])[CH2:3]1)=[O:21])([CH3:18])([CH3:17])[CH3:16]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 232933-HydroxypiperidineHCID 10219638Carbonic acid, bis(1,1-dimethylethyl) ester

Product 1

HCID 5456991-Boc-3-hydroxypiperidineYield 87%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 10.0 g (72.67 mmol) 3-hydroxypiperidine in 100 mL dry THF at 0° C. was added 10.1 mL (72.67 mmol) NEt3 and 15.86 g (72.67 mmol) di-t-butylcarbonate in 100 mL THF and the reaction allowed to warm to rt and stirred overnight. The solvent was removed under reduced pressure, the resulting residue dissolved in 300 mL CH2Cl2 and the solution extracted with H2O (2×200 mL), dried over MgSO4, filtered and rotary evaporated to yield 12.66 g (87%) of N-(t-butoxycarbonyl)-3-piperidinol as an oil which slowly solidified to a white solid.

Workup

  1. customThe solvent was removed under reduced pressure
  2. dissolutionthe resulting residue dissolved in 300 mL CH2Cl2
  3. extractionthe solution extracted with H2O (2×200 mL)
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customrotary evaporated

Sources & evidence

ORD record
ord-3aec8cf498b9454ebb3ae0c0dfc57abc
Source dataset
uspto-grants-2003_02
Patent number
US06518285B2

Reaction notes

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