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

HRID 1253505Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1253505
[CH:1]([CH:3]1[CH2:6][N:5]([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[CH2:4]1)=O.[C:14](=O)([O-])[O-].[K+].[K+].CC(C)C(=O)C(P(=O)([O-])[O-])=[N+]=[N-]>CO>[C:1]([CH:3]1[CH2:6][N:5]([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[CH2:4]1)#[CH:14]

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 10726182Tert-butyl 3-formylazetidine-1-carboxylateHCID 86586111Dimethyl-1-diazo-2-oxopropylphosphonate

Produkt 1

HCID 54349237tert-Butyl 3-ethynylazetidine-1-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel2×

Versuchsvorschrift

To a solution of tert-butyl 3-formylazetidine-1-carboxylate (96 g, 0.46 mol) and potassium carbonate (128 g, 0.924 mol) in methanol was added dropwise dimethyl-1-diazo-2-oxopropylphosphonate (67 g, 0.35 mol) in 1.6 L of methanol. The mixture was stirred for 2 h and filtered. The filtrate was concentrated and the residue was diluted with 800 ml of methyl-tert-butyl ether and 1 L of 5% w/w aqueous sodium bicarbonate. The layers were separated and the aqueous layer was washed with methyl-tert-butyl ether (2×500 ml). The combined organic layers were dried over magnesium sulfate, filtered and concentrated. The residue was purified by flash column chromatography to afford tert-butyl 3-ethynylazetidine-1-carboxylate.

Aufarbeitung

  1. filtrationfiltered
  2. concentrationThe filtrate was concentrated
  3. additionthe residue was diluted with 800 ml of methyl-tert-butyl ether and 1 L of 5% w/w aqueous sodium bicarbonate
  4. customThe layers were separated
  5. washthe aqueous layer was washed with methyl-tert-butyl ether (2×500 ml)
  6. dry with materialThe combined organic layers were dried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe residue was purified by flash column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-dfb4335b6e2e4d2497d86542d92c645d
Quelldatensatz
uspto-grants-2013_06
Patentnummer
US08455477B2

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