Methanesulfonyl chloride → (S)-1-Benzyl-3-mesyloxypyrrolidine

HRID 1597451

Reaktionsgleichung

Reaktionsgleichung von HRID 1597451
[CH2:1]([N:8]1[CH2:12][CH2:11][C@H:10]([OH:13])[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:14][S:15](Cl)(=[O:17])=[O:16]>N1C=CC=CC=1>[CH3:14][S:15]([O:13][C@H:10]1[CH2:11][CH2:12][N:8]([CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[CH2:9]1)(=[O:17])=[O:16]

Komponenten

4

Edukt 2

HCID 31297Methanesulfonyl chlorideHCID 2733875(S)-(-)-1-Benzyl-3-pyrrolidinol

Produkt 1

HCID 10934081(S)-1-Benzyl-3-mesyloxypyrrolidineAusbeute 44,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1049PyridineLösungsmittel

Versuchsvorschrift

To (S)(−)-1-benzyl-3-pyrrolidinol (5 g, 28.2 mmol) in pyridine (40 mL) was added methane sulphonyl chloride (2.03 mL, 26.2 mmol, 0.93 equiv.) dropwise. The reaction mixture stirred 3 h, was poured into ice water (100 mL) and extracted with DCM (3×50 mL). The combined organic extracts were washed with saturated aq NaHCO3, brine and dried (MgSO4) to give 3 g of the titled compound: low resolution MS (ES) m/e 256.0 (MH+).

Aufarbeitung

  1. extractionextracted with DCM (3×50 mL)
  2. washThe combined organic extracts were washed with saturated aq NaHCO3, brine
  3. dry with materialdried (MgSO4)

Quellen und Nachweise

ORD-Eintrag
ord-6a2f4d1b51fd4b608002352170459363
Quelldatensatz
uspto-grants-2001_09
Patentnummer
US06294580B1

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