Itaconic acid → 1-Cyclohexyl-5-oxopyrrolidine-3-carboxylic acid

HRID 2235178

Reaktionsgleichung

Reaktionsgleichung von HRID 2235178
[CH2:1]=[C:2]([CH2:6][C:7]([OH:9])=O)[C:3]([OH:5])=[O:4].[CH:10]1([NH2:16])[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]1>>[CH:10]1([N:16]2[C:7](=[O:9])[CH2:6][CH:2]([C:3]([OH:5])=[O:4])[CH2:1]2)[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]1

Komponenten

3

Edukt 2

HCID 811Itaconic acidHCID 7965Cyclohexylamine

Produkt 1

HCID 2385461-Cyclohexyl-5-oxopyrrolidine-3-carboxylic acidAusbeute 96,5 %

Versuchsvorschrift

Place 2-methylene-succinic acid (12.0 g, 92.2 mmol) and cyclohexylamine (9.15 g, 92.2 mmol) and heat to 160° C. for hours. Cool to give 18.8 g (96%) of 1-cyclohexyl-5-oxo-pyrrolidine-3-carboxylic acid. Charge a flask with 1-cyclohexyl-5-oxo-pyrrolidine-3-carboxylic acid (16.2 g, 76.7 mmol), add methylene chloride (20 mL) and cool to 0° C. Slowly add borane in THF (1M, 115.1 mL, 115.1 mmol) and stir for two hours at 0° C. Quench the reaction with ice and extract with methylene chloride. Dry over sodium sulfate, filter, and concentrate. Purify by silica gel (1-5% methanol in methylene chloride) to yield 9.9 g (65%) of the title compound: Mass spectrum (apci) m/z=198.1 (M+H).

Aufarbeitung

  1. temperatureCool

Quellen und Nachweise

ORD-Eintrag
ord-0855fb392fa64fb09c58c6816ab9c216
Quelldatensatz
uspto-grants-2010_05
Patentnummer
US07713979B2

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