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

HRID 528775

Reaction equation

HRID 528775 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][CH:10]([CH:13]=O)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH2:15](OP(C(=[N+]=[N-])C(=O)C)(=O)OCC)C.C([O-])([O-])=O.[K+].[K+]>CO>[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][CH:10]([C:13]#[CH:15])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 4692112(+-)-1-(tert-Butoxycarbonyl)pyrrolidine-3-carboxaldehydeHCID 136104435(1Z)-1-diazo-1-diethoxyphosphorylpropan-2-one

Product 1

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

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To 1.23 g (6.17 mmol) 3-Formyl-pyrrolidine-1-carboxylic acid tert-butyl ester in 30 mL dry MeOH was added at room temperature 1.42 g (7.41 mmol) (1-Diazo-2-oxo-propyl)-phosphonic acid diethyl ester and 1.71 g (12.4 mmol) K2CO3 and stirring was continued for 2 h. 10 g of silica gel was added to the reaction mixture, stirring continued for 20 min and then filtered. After evaporation of the solvent the residue was purified by column chromatography (silica, cyclohexane/EtOAc 1:1).

Workup

  1. addition10 g of silica gel was added to the reaction mixture
  2. stirringstirring
  3. waitcontinued for 20 min
  4. filtrationfiltered
  5. customAfter evaporation of the solvent the residue
  6. customwas purified by column chromatography (silica, cyclohexane/EtOAc 1:1)

Sources & evidence

ORD record
ord-b66536a3de4d4670aac403b60817204e
Source dataset
uspto-grants-2016_05
Patent number
US09346816B2

Linked notes

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