Methanesulfonyl chloride → Tert-butyl (3R)-3-(methanesulfonyloxy)pyrrolidine-1-carboxylate

HRID 472888

Reaktionsgleichung

Reaktionsgleichung von HRID 472888
[OH:1][C@@H:2]1[CH2:6][CH2:5][N:4]([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[CH2:3]1.[CH3:14][S:15](Cl)(=[O:17])=[O:16]>>[CH3:14][S:15]([O:1][C@@H:2]1[CH2:6][CH2:5][N:4]([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[CH2:3]1)(=[O:17])=[O:16]

Komponenten

3

Edukt 2

HCID 31297Methanesulfonyl chlorideHCID 6544479tert-Butyl (3R)-3-hydroxypyrrolidine-1-carboxylate2×

Produkt 1

HCID 10934372Tert-butyl (3R)-3-(methanesulfonyloxy)pyrrolidine-1-carboxylate

Versuchsvorschrift

The preparation of compound 9 is outlined in Scheme 1. Commercially available tert-butyl (R)-3-hydroxypyrrolidine-1-carboxylate (compound 1) is treated with methanesulfonyl chloride to give tert-butyl (R)-3-(methylsulfonyloxy)pyrrolidine-1-carboxylate (compound 2), which then is reacted with diethylmalonate and a suitable base (e.g., potassium tert-butoxide or sodium ethoxide) to give diethyl (R)-2-(1-(tert-butoxycarbonyl)pyrrolidin-3-yl)malonate (compound 3) with inverted stereochemistry around the chiral carbon.

Quellen und Nachweise

ORD-Eintrag
ord-7dcb9650998544019e90ad5851198821
Quelldatensatz
uspto-grants-2014_01
Patentnummer
US08633227B2

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