Citric Acid → (3S)-1-(methylsulfonyl)pyrrolidin-3-yl methanesulfonate

HRID 2280652Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2280652
Cl.[OH:2][C@H:3]1[CH2:7][CH2:6][NH:5][CH2:4]1.C(N(CC)CC)C.[CH3:15][S:16](Cl)(=[O:18])=[O:17].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>ClCCl>[CH3:15][S:16]([O:2][C@H:3]1[CH2:7][CH2:6][N:5]([S:16]([CH3:15])(=[O:18])=[O:17])[CH2:4]1)(=[O:18])=[O:17]

Komponenten

6

Edukt 4

HCID 311Citric AcidHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 22309122(S)-3-Hydroxypyrrolidine hydrochloride

Produkt 1

HCID 59816083(3S)-1-(methylsulfonyl)pyrrolidin-3-yl methanesulfonateAusbeute 62,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

The crude (S)-3-hydroxyl-pyrrolidine hydrochloride 11b (124 mg, 1 mmol) was dissolved in 15 mL of dichloromethane, followed by addition of triethylamine (303 mg, 3 mmol). The reaction solution was cooled down to 0° C., followed by addition of methanesulfonyl chloride (264 mg, 2.30 mmol), then warmed up to room temperature and stirred for another 2.5 hours. The resulting solution was mixed with 10 mL of dichloromethane, 1M citric acid was added dropwise to adjust the pH to 4˜5, the organic phase was dried with anhydrous magnesium sulphate and filtered. The filtrate was concentrated under reduced pressure to obtain the crude title compound (S)-1-(methylsulfonyl)pyrrolidin-3-yl methanesulfonate 11c (153 mg) as a yellow solid, which was directly used in the next step without further purification.

Aufarbeitung

  1. temperaturewarmed up to room temperature
  2. additionwas added dropwise
  3. dry with materialthe organic phase was dried with anhydrous magnesium sulphate
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-4da8a0012f1642619cb96cd2ffb31fad
Quelldatensatz
uspto-grants-2015_09
Patentnummer
US09139548B2

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