Water → tert-Butyl 3-{[(4-methylbenzene-1-sulfonyl)oxy]methyl}pyrrolidine-1-carboxylate

HRID 358901Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 358901
[C:1]1([CH3:11])[CH:6]=[CH:5][C:4]([S:7](Cl)(=[O:9])=[O:8])=[CH:3][CH:2]=1.[C:12]([O:16][C:17]([N:19]1[CH2:23][CH2:22][CH:21]([CH2:24][OH:25])[CH2:20]1)=[O:18])([CH3:15])([CH3:14])[CH3:13].O>N1C=CC=CC=1>[C:12]([O:16][C:17]([N:19]1[CH2:23][CH2:22][CH:21]([CH2:24][O:25][S:7]([C:4]2[CH:5]=[CH:6][C:1]([CH3:11])=[CH:2][CH:3]=2)(=[O:9])=[O:8])[CH2:20]1)=[O:18])([CH3:15])([CH3:14])[CH3:13]

Komponenten

5

Edukt 3

HCID 962WaterHCID 73974-Toluenesulfonyl chlorideHCID 5237175tert-Butyl 3-(hydroxymethyl)pyrrolidine-1-carboxylate

Produkt 1

HCID 20067158tert-Butyl 3-{[(4-methylbenzene-1-sulfonyl)oxy]methyl}pyrrolidine-1-carboxylateAusbeute 72 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1049PyridineLösungsmittel

Versuchsvorschrift

30.0 g (0.157 mole) of p-toluenesulfonyl chloride were added to a solution of 29.5 g (0.143 mole) of 1-t-butoxycarbonyl-3-hydroxymethylpyrrolidine [prepared as described in Step (2) above] dissolved in 500 ml of pyridine. The mixture was then stirred for 5 hours whilst ice-cooling, after which it was stirred at room temperature overnight. The reaction mixture was poured into 1 liter of water and then extracted with ethyl acetate. The extract was washed with water, dried and concentrated under by evaporation reduced pressure. The residue was subjected to column chromatography through silica gel eluted with a 1:4 by volume mixture of ethyl acetate and toluene, to give 36.6 g of 1-t-butoxycarbonyl-3-(p-toluenesulfonyloxymethyl)pyrrolidine as a pale brown oil, which gradually crystallized.

Aufarbeitung

  1. temperaturecooling
  2. stirringafter which it was stirred at room temperature overnight
  3. extractionextracted with ethyl acetate
  4. washThe extract was washed with water
  5. customdried
  6. concentrationconcentrated under by evaporation reduced pressure
  7. washeluted with a 1:4 by volume mixture of ethyl acetate and toluene

Quellen und Nachweise

ORD-Eintrag
ord-3fdd1c4a913a434fb4fc8e7acf9c1f91
Quelldatensatz
uspto-grants-1991_03
Patentnummer
US04997943

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