Potassium Carbonate → Tert-butyl 4-ethynyl-4-hydroxypiperidine-1-carboxylate

HRID 1694877Notes

Reaction equation

HRID 1694877 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11]([OH:20])([C:14]#[C:15][Si](C)(C)C)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+]>CO>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11]([C:14]#[CH:15])([OH:20])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 108039811,1-Dimethylethyl 4-hydroxy-4-[(trimethylsilyl)ethynyl]-1-piperidinecarboxylate

Product 1

HCID 18366117Tert-butyl 4-ethynyl-4-hydroxypiperidine-1-carboxylateYield 86%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of the 4-Hydroxy-4-trimethylsilanylethynyl piperidine-1-carboxylic acid tert-butyl ester (7 g, 23.5 mmol, 1 eq) and potassium carbonate (1.0 g, 7.25 mmol, 0.3 eq) in MeOH (30 ml) were stirred for 6 h at room temperature. After this time, the solvent was removed under reduced pressure and the residue suspended in diethyl ether. The suspension was washed with saturated ammonium chloride and water and dried over MgSO4. After filtering, the filtrate was evaporated to give the product (4.5 g, 86%) as a white solid.

Workup

  1. customAfter this time, the solvent was removed under reduced pressure
  2. washThe suspension was washed with saturated ammonium chloride and water
  3. dry with materialdried over MgSO4
  4. filtrationAfter filtering
  5. customthe filtrate was evaporated

Sources & evidence

ORD record
ord-e8535a47429c40678c915f9fbc1bf7f7
Source dataset
uspto-grants-2012_04
Patent number
US08158797B2

Reaction notes

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