Hydrochloric Acid → (2S)-1-allyloxycarbonyl-2-hydroxymethyl-4-methylenepyrrolidine
Reaktionsgleichung
[CH2:1]([O:4][C:5]([N:7]1[CH2:11][C:10](=[CH2:12])[CH2:9][C@H:8]1[CH2:13][O:14][Si](C(C)(C)C)(C)C)=[O:6])[CH:2]=[CH2:3].Cl.C(=O)([O-])[O-].[K+].[K+]>C(OCC)(=O)C.[Cl-].[Na+].O>[CH2:1]([O:4][C:5]([N:7]1[CH2:11][C:10](=[CH2:12])[CH2:9][C@H:8]1[CH2:13][OH:14])=[O:6])[CH:2]=[CH2:3]Komponenten
6
Edukt 3
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 2
Versuchsvorschrift
To a solution of (2S)-1-allyloxycarbonyl-2-(t-butyldimethylsilyloxymethyl)-4-methylenepyrrolidine (2.88 g) in ethyl acetate (100 ml) was added 6N hydrochloric acid (3.0 ml) at ambient temperature. After stirring for 1 hour at ambient temperature, to the mixture were added potassium carbonate (2.54 g) and brine (30 ml) with stirring. The organic layer was separated, washed in turn with aqueous sodium hydrogen carbonate and brine, dried over magnesium sulfate and evaporated. The residue was chromatographed on silica gel (40 ml) eluting with a mixture of n-hexane and ethyl acetate (3:1 V/V) to give (2S)-1-allyloxycarbonyl-2-hydroxymethyl-4-methylenepyrrolidine (1.78 g).
Aufarbeitung
- stirringwith stirring
- customThe organic layer was separated
- washwashed in turn with aqueous sodium hydrogen carbonate and brine
- dry with materialdried over magnesium sulfate
- customevaporated
- customThe residue was chromatographed on silica gel (40 ml)
- washeluting with a mixture of n-hexane and ethyl acetate (3:1 V/V)
Quellen und Nachweise
- ORD-Eintrag
- ord-28a56fcf8deb4b3ab3d934a3002939a7
- Quelldatensatz
- uspto-grants-1990_05
- Patentnummer
- US04923857
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