Potassium Carbonate → tert-Butyl 4-ethynylpiperidine-1-carboxylate

HRID 871072Notes

Reaction equation

HRID 871072 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+].[N+](=C(P(=O)(OC)OC)C(=O)C)=[N-]>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 11430Potassium CarbonateHCID 1514430tert-Butyl 4-formylpiperidine-1-carboxylateHCID 136023029(1E)-1-diazo-1-dimethoxyphosphorylpropan-2-one

Product 1

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

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of Example 1C (1 g, 4.69 mmol) in methanol (20 mL) was added potassium carbonate (3.89 g, 28.1 mmol) and the mixture was stirred for 30 minutes. Dimethyl 1-diazo-2-oxopropylphosphonate (3.60 g, 18.76 mmol) was added and the mixture was stirred for 12 hours. The mixture was filtered through diatomaceous earth with methanol, concentrated and purified by column chromatography on silica gel (Isco®, Redi-Sep® column), eluting with 15% ethyl acetate in hexane to afford the title compound. LCMS: 110 (M+H-Boc)+.

Workup

  1. stirringthe mixture was stirred for 12 hours
  2. filtrationThe mixture was filtered through diatomaceous earth with methanol
  3. concentrationconcentrated
  4. custompurified by column chromatography on silica gel (Isco®, Redi-Sep® column)
  5. washeluting with 15% ethyl acetate in hexane

Sources & evidence

ORD record
ord-0fd9e927093d43fa9d60044fbf5eec08
Source dataset
uspto-grants-2015_03
Patent number
US08969375B2

Reaction notes

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