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

HRID 1038040Notes

Reaction equation

HRID 1038040 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([CH:14]=O)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:16](=O)([O-])[O-].[K+].[K+].COP(C(=[N+]=[N-])C(=O)C)(=O)OC>CO>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]#[CH:16])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

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-carboxylateYield 88%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

At 0 C, to a stirred mixture of 4-formyl-piperidine-1-carboxylic acid tert-butyl ester (358 mg, 1.68 mmols) and potassium carbonate (464 mg, 3.36 mmols) in methanol (16 ml) was added dropwise a solution of (1-diazo-2-oxo-propyl)-phosphonic acid dimethyl ester (323 mg, 1.68 mmols) in methanol (2 ml). The resulting mixture was stirred at room temperature overnight, filtered and concentrated. The residue was chromatographed on silica gel using a solution of ethyl acetate in hexanes (1:5) to provide the title compound (308 mg, 88%) as colorless crystals. LCMS m/e (154, M-t-Bu+2H). (J. Am. Chem. Soc. 2003, 125, 3714.)

Workup

  1. filtrationfiltered
  2. concentrationconcentrated
  3. customThe residue was chromatographed on silica gel using a solution of ethyl acetate in hexanes (1:5)

Sources & evidence

ORD record
ord-7c4b986333ea4476910459ae598f5114
Source dataset
uspto-grants-2013_10
Patent number
US08546404B2

Reaction notes

Loading…