Potassium Carbonate → HCID 86731563, compound

HRID 1430579Notes

Reaction equation

HRID 1430579 reaction equation
[C:1](=O)([O-])[O-].[K+].[K+].[N+](=C(P(=O)(OC)OC)C(=O)C)=[N-].[CH3:19][C@H:20]1[N:25]([C:26]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=2[N:34]2[N:38]=[CH:37][CH:36]=[N:35]2)=[O:27])[CH2:24][C@H:23]([CH:39]=O)[CH2:22][CH2:21]1>CO>[C:39]([C@H:23]1[CH2:24][N:25]([C:26]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=2[N:34]2[N:38]=[CH:37][CH:36]=[N:35]2)=[O:27])[C@H:20]([CH3:19])[CH2:21][CH2:22]1)#[CH:1]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 86731562HCID 86731562, compoundHCID 136023029(1E)-1-diazo-1-dimethoxyphosphorylpropan-2-one

Product 1

HCID 86731563HCID 86731563, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Conditions

Temperature
0 °C

Procedure

A mixture of potassium carbonate (0.556 g, 4.02 mmol) and dimethyl (1-diazo-2-oxopropyl)phosphonate (0.837 g, 4.36 mmol) in methanol (35 mL) under an atmosphere of nitrogen was cooled to 0° C. To this mixture was added a solution of (3R,6R)-6-methyl-1-{[2-(2H-1,2,3-triazol-2-yl)phenyl]carbonyl}piperidine-3-carbaldehyde (1.00 g, 3.35 mmol) in methanol (12 mL) dropwise. The reaction was allowed to warm slowly to RT and stir for 17 h. The mixture was concentrated in vacuo, treated with water, and extracted with ethyl acetate. The organic fraction was washed with water and brine, dried over sodium sulfate, filtered, and concentrated in vacuo. The resultant residue was purified via silica gel chromatography eluting with 0-50% ethyl acetate in hexanes to provide [(2R,5S)-5-ethynyl-2-methylpiperidin-1-yl][2-(2H-1,2,3-triazol-2-yl)phenyl]methanone which gave a proton NMR spectra consistent with theory and a mass ion (ES+) of 295.3 for M+H+, and [(2R,5R)-5-ethynyl-2-methylpiperidin-1-yl][2-(2H-1,2,3-triazol-2-yl)phenyl]methanone which gave a proton NMR spectra consistent with theory and a mass ion (ES+) of 295.2 for M+H+.

Workup

  1. temperatureto warm slowly to RT
  2. concentrationThe mixture was concentrated in vacuo
  3. additiontreated with water
  4. extractionextracted with ethyl acetate
  5. washThe organic fraction was washed with water and brine
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe resultant residue was purified via silica gel chromatography
  10. washeluting with 0-50% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-40cc9cbb668748048b15f8b1e3b4d278
Source dataset
uspto-grants-2015_01
Patent number
US08940898B2

Reaction notes

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