Potassium Carbonate → tert-Butyl 3-ethynylpyrrolidine-1-carboxylate

HRID 1253516Notes

Reaction equation

HRID 1253516 reaction equation
[CH:1]([CH:3]1[CH2:7][CH2:6][N:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:4]1)=O.[C:15](=O)([O-])[O-].[K+].[K+]>CO>[C:1]([CH:3]1[CH2:7][CH2:6][N:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:4]1)#[CH:15]

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 4692112(+-)-1-(tert-Butoxycarbonyl)pyrrolidine-3-carboxaldehyde

Product 1

HCID 54012212tert-Butyl 3-ethynylpyrrolidine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Dimethyl-1-diazo-2-oxypropylphosphonate (11.5 g, 60 mmol) was added to a solution of tert-butyl 3-formylpyrrolidine-1-carboxylate (10 g, 50 mmol) and potassium carbonate (13.8 g, 100 mmol) in dry methanol (150 mL). After 16 hours, the reaction mixture was filtered and washed with methanol. The filtrate was extracted with diethyl ether, and the organic layer was washed with 5% aqueous sodium bicarbonate, dried over sodium sulfate, filtered, and concentrated in vacuo. The residue was purified by column chromatography on silica gel to afford tert-butyl 3-ethynylpyrrolidine-1-carboxylate.

Workup

  1. filtrationthe reaction mixture was filtered
  2. washwashed with methanol
  3. extractionThe filtrate was extracted with diethyl ether
  4. washthe organic layer was washed with 5% aqueous sodium bicarbonate
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-cb1cd139876b4f2788276e9c69892b2d
Source dataset
uspto-grants-2013_06
Patent number
US08455477B2

Reaction notes

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