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

HRID 528775

Reaktionsgleichung

Reaktionsgleichung von HRID 528775
[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]

Komponenten

5

Edukt 3

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

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).

Aufarbeitung

  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)

Quellen und Nachweise

ORD-Eintrag
ord-b66536a3de4d4670aac403b60817204e
Quelldatensatz
uspto-grants-2016_05
Patentnummer
US09346816B2

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