Triethylamine → (S)-tert-butyl (1-(methylsulfonyl)pyrrolidin-3-yl)carbamate

HRID 926719Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 926719
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[NH:6]1[CH2:10][CH2:9][C@H:8]([NH:11][C:12](=[O:18])[O:13][C:14]([CH3:17])([CH3:16])[CH3:15])[CH2:7]1.CCN(CC)CC>C(Cl)Cl>[CH3:1][S:2]([N:6]1[CH2:10][CH2:9][C@H:8]([NH:11][C:12](=[O:18])[O:13][C:14]([CH3:16])([CH3:15])[CH3:17])[CH2:7]1)(=[O:4])=[O:3]

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 1514396(3S)-(-)-3-(tert-Butoxycarbonylamino)pyrrolidine

Produkt 1

HCID 58959879(S)-tert-butyl (1-(methylsulfonyl)pyrrolidin-3-yl)carbamateAusbeute 58,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

Methane sulfonyl chloride (204 mg, 1.78 mmol) was added to a solution of (S)-tert-butyl pyrrolidin-3-ylcarbamate (300 mg, 1.62 mmol) and Et3N (197 mg, 1.94 mmol) in DCM (6 mL) at 0-5° C.; stirring was continued at 20-35° C. for 2 h. The reaction mixture was diluted with DCM, washed with water, aqueous NaHCO3 solution followed by brine to afford 250 mg of the title compound.

Aufarbeitung

  1. washwashed with water, aqueous NaHCO3 solution

Quellen und Nachweise

ORD-Eintrag
ord-cb59217d36284eafb639bcaa1a0fd602
Quelldatensatz
uspto-grants-2016_03
Patentnummer
US09289419B2

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