Hydrochloric Acid → 1-Allyloxycarbonyl-3-hydroxymethylpyrrolidine

HRID 1650289

Reaktionsgleichung

Reaktionsgleichung von HRID 1650289
[CH2:1]([O:4][C:5]([N:7]1[CH2:11][CH2:10][CH:9]([CH2:12][O:13][Si](C(C)(C)C)(C)C)[CH2:8]1)=[O:6])[CH:2]=[CH2:3].Cl.C[O-].[Na+]>CO>[CH2:1]([O:4][C:5]([N:7]1[CH2:11][CH2:10][CH:9]([CH2:12][OH:13])[CH2:8]1)=[O:6])[CH:2]=[CH2:3]

Komponenten

5

Edukt 3

HCID 313Hydrochloric AcidHCID 10942334Sodium MethoxideHCID 199149161-Allyloxycarbonyl-3-t-butyldimethylsilyloxymethylpyrrolidine

Produkt 1

HCID 151171941-Allyloxycarbonyl-3-hydroxymethylpyrrolidineAusbeute 102,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel2×

Versuchsvorschrift

A solution of 1-allyloxycarbonyl-3-t-butyldimethylsilyloxymethylpyrrolidine (29.95 g) in a mixture of concentrated hydrochloric acid (15 ml) and methanol (150 ml) was stirred at ambient temperature for one hour. A 28% solution of sodium methoxide in methanol (35 ml) was added to the mixture. Insoluble material was filtered off and the filtrate was concentrated under reduced pressure to give a syrup. The syrup was subjected to a column chromatography on silica gel (400 g) and eluted with ethyl acetate to give 1-allyloxycarbonyl-3-hydroxymethylpyrrolidine (19.01 g).

Aufarbeitung

  1. filtrationInsoluble material was filtered off
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customto give a syrup
  4. washeluted with ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-986e32bc0752402590509166880e43ad
Quelldatensatz
uspto-grants-1990_05
Patentnummer
US04923857

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