Water → tert-Butyl 4-ethynylpiperidine-1-carboxylate

HRID 522213Notes

Reaction equation

HRID 522213 reaction equation
[CH:1]([CH:3]1[CH2:8][CH2:7][N:6]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:5][CH2:4]1)=O.[C:16](=O)([O-])[O-].[K+].[K+].O>CO>[C:1]([CH:3]1[CH2:8][CH2:7][N:6]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:5][CH2:4]1)#[CH:16]

Participants

5

Reactant 3

HCID 962WaterHCID 11430Potassium CarbonateHCID 1514430tert-Butyl 4-formylpiperidine-1-carboxylate

Product 1

HCID 15550481tert-Butyl 4-ethynylpiperidine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To a solution of tert-butyl 4-formylpiperidine-1-carboxylate (2.2 g, 10.4 mmol) and potassium carbonate (2.9 g, 20.8 mmol) in methanol (100 mL) was added Example 21A (2.0 g, 10.4 mmol) in methanol (20 mL) and the mixture was stirred at room temperature overnight. Water was added and the mixture was extracted with ethyl acetate (twice). The combined organic layers were washed with brine and concentrated. Purification by flash chromatography on silica gel (Teledyne CombiFlash Rf, 1:5 ethyl acetate/hexane) gave the title compound. MS (DCI/NH3) m/z 210 (M+H)+.

Workup

  1. extractionthe mixture was extracted with ethyl acetate (twice)
  2. washThe combined organic layers were washed with brine
  3. concentrationconcentrated
  4. customPurification by flash chromatography on silica gel (Teledyne CombiFlash Rf, 1:5 ethyl acetate/hexane)

Sources & evidence

ORD record
ord-0660614bf5af493682a5ec6cec2cdaf5
Source dataset
uspto-grants-2016_05
Patent number
US09328112B2

Reaction notes

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