4-Chlorobenzenesulfonyl chloride → (2S,4R)-1-allyloxycarbonyl-2-p-chlorobenzenesulfonyloxy methyl-4-methanesulfonyloxypyrrolidine

HRID 1034523Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1034523
[CH2:1]([O:4][C:5]([N:7]1[CH2:11][C@H:10]([O:12][S:13]([CH3:16])(=[O:15])=[O:14])[CH2:9][C@H:8]1[CH2:17][OH:18])=[O:6])[CH:2]=[CH2:3].[Cl:19][C:20]1[CH:25]=[CH:24][C:23]([S:26](Cl)(=[O:28])=[O:27])=[CH:22][CH:21]=1.C(N(CC)CC)C>ClCCl>[CH2:1]([O:4][C:5]([N:7]1[CH2:11][C@H:10]([O:12][S:13]([CH3:16])(=[O:14])=[O:15])[CH2:9][C@H:8]1[CH2:17][O:18][S:26]([C:23]1[CH:24]=[CH:25][C:20]([Cl:19])=[CH:21][CH:22]=1)(=[O:28])=[O:27])=[O:6])[CH:2]=[CH2:3]

Komponenten

5

Edukt 3

HCID 73984-Chlorobenzenesulfonyl chlorideHCID 8471TriethylamineHCID 18639172(2S,4R)-1-allyloxycarbonyl-4-methanesulfonyloxypyrrolidine-2-methanol

Produkt 1

HCID 22851791(2S,4R)-1-allyloxycarbonyl-2-p-chlorobenzenesulfonyloxy methyl-4-methanesulfonyloxypyrrolidineAusbeute 105 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

To a solution of (2S,4R)-1-allyloxycarbonyl-4-methanesulfonyloxypyrrolidine-2-methanol (13.4 g: 50 mmole) in dichloromethane (50 ml), p-chlorobenzenesulfonyl chloride (12.66 g: 60 mmole) is added in a nitrogen atmosphere at room temperature and a solution of triethylamine (8.69 ml: 62.5 mmole) in dichloromethane (10 ml) is further added dropwise. The mixture is stirred at room temperature overnight. The reaction mixture is successively washed with aqueous sodium hydrogen carbonate and saturated brine, dried over magnesium sulfate, concentrated in vacuo, and purified by silica gel chromatography (toluene-ethyl acetate) to give crude (2S,4R)-1-allyloxycarbonyl-2-p-chlorobenzenesulfonyloxy methyl-4-methanesulfonyloxypyrrolidine (23.73 g) as oil. Yield: 105%. NMR δ(CDCl3) ppm: 2.2 to 2.6(m, 2H), 3.04(s, 3H), 3.58(dd, J=5.0 Hz, J=11.4 Hz, 1H), 3.8 to 4.0(m, 1H), 4.1 to 4.3(m, 3H), 4.5(m, 3H), 5.1 to 5.4(m, 3H), 5.7 to 6.0(m, 1H).

Aufarbeitung

  1. washThe reaction mixture is successively washed with aqueous sodium hydrogen carbonate and saturated brine
  2. dry with materialdried over magnesium sulfate
  3. concentrationconcentrated in vacuo
  4. custompurified by silica gel chromatography (toluene-ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-3fe3c5b84df9490392b37b8fec117244
Quelldatensatz
uspto-grants-1994_05
Patentnummer
US05317016

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