Hydrochloric Acid → (S)-3-(Toluene-4-sulfonyloxy)-pyrrolidine-1-carboxylic acid tert-butyl ester

HRID 69513

Reaktionsgleichung

[C:1]1([CH3:11])[CH:6]=[CH:5][C:4]([S:7](Cl)(=[O:9])=[O:8])=[CH:3][CH:2]=1.[C:12]([O:16][C:17]([N:19]1[CH2:23][CH2:22][C@H:21]([OH:24])[CH2:20]1)=[O:18])([CH3:15])([CH3:14])[CH3:13].C(N(CC)CC)C.Cl>C(Cl)Cl.CN(C1C=CN=CC=1)C>[C:12]([O:16][C:17]([N:19]1[CH2:23][CH2:22][C@H:21]([O:24][S:7]([C:4]2[CH:5]=[CH:6][C:1]([CH3:11])=[CH:2][CH:3]=2)(=[O:9])=[O:8])[CH2:20]1)=[O:18])([CH3:15])([CH3:13])[CH3:14]

Komponenten

Reaktionsbedingungen

Temperatur: 0 °C

Versuchsvorschrift

To a mixture of p-toluenesulfonyl chloride (10.0 g) in dry methylene chloride (40 mL) was added at 0° C. a solution of (S)-3-Hydroxy-pyrrolidine-1-carboxylic acid tert-butyl ester (2.8 g) in dry methylene chloride (15 mL). DMAP (1.1 g) and triethylamine (6.1 g) was added. The mixture was stirred at 0° C. for 3 h. The reaction mixture was then allowed to reach room temperature and stirred for 12 h. The mixture was acidified with 1 N HCl. The organic layer was washed two times with 1 N HCl, one time with saturated sodium hydrogen carbonate solution and one time with brine. The organic layers were dried over sodium sulfate and concentrated. The product with the molecular weight of 341.43 (C16H23NO5S) was obtained in this way; MS (ESI): 342 (M+H+).

Aufarbeitung

customto reach room temperature
stirringstirred for 12 h
washThe organic layer was washed two times with 1 N HCl, one time with saturated sodium hydrogen carbonate solution and one time with brine
dry with materialThe organic layers were dried over sodium sulfate
concentrationconcentrated
customThe product with the molecular weight of 341.43 (C16H23NO5S) was obtained in this way

Quellen und Nachweise

ORD-Eintrag: ord-d8cf54f57ee94f80a5892740a783cffd
Quelldatensatz: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08822495B2

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