Hydrochloric Acid → 1-(4-Toluenesulfonyl)-2-(4-toluenesulfonyloxymethyl)-4-(4-toluenesulfonyloxy)-pyrrolidine

HRID 1031562Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1031562
[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]1([CH3:39])[CH:17]=[CH:16][C:15]([S:18]([N:21]2[CH2:25][CH:24]([O:26][S:27]([C:30]3[CH:35]=[CH:34][C:33]([CH3:36])=[CH:32][CH:31]=3)(=[O:29])=[O:28])[CH2:23][CH:22]2[CH2:37][OH:38])(=[O:20])=[O:19])=[CH:14][CH:13]=1.Cl>N1C=CC=CC=1>[C:12]1([CH3:39])[CH:13]=[CH:14][C:15]([S:18]([N:21]2[CH2:25][CH:24]([O:26][S:27]([C:30]3[CH:35]=[CH:34][C:33]([CH3:36])=[CH:32][CH:31]=3)(=[O:29])=[O:28])[CH2:23][CH:22]2[CH2:37][O:38][S:7]([C:4]2[CH:5]=[CH:6][C:1]([CH3:11])=[CH:2][CH:3]=2)(=[O:9])=[O:8])(=[O:19])=[O:20])=[CH:16][CH:17]=1

Komponenten

5

Edukt 3

HCID 313Hydrochloric AcidHCID 73974-Toluenesulfonyl chlorideHCID 145411981-(4-Toluenesulfonyl)-2-hydroxymethyl-4-(4-toluenesulfonyloxy)-pyrrolidine

Produkt 1

HCID 2961001-(4-Toluenesulfonyl)-2-(4-toluenesulfonyloxymethyl)-4-(4-toluenesulfonyloxy)-pyrrolidineAusbeute 85 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1049PyridineLösungsmittel

Versuchsvorschrift

To a cooled solution of 1.83 g (9.6 mmoles) 4-toluenesulfonyl chloride in 10 mL pyridine at +10° C. was added 3.40 g (8 mmoles) of 1-(4-toluenesulfonyl)-2-hydroxymethyl-4-(4-toluenesulfonyloxy)-pyrrolidine and the mixture was stirred 18 hours. The solution obtained was then poured into 50 mL ice-cooled 2N hydrochloric acid. The precipitate was filtered, washed with water and ether. The crystalline product was purified in boiling water and ether. The crystalline product was purified in boiling ethanol to give 3.94 g of titled compound. MP 153° C. [α]D =+46.7° (c=1.9, acetone).

Aufarbeitung

  1. customThe solution obtained
  2. filtrationThe precipitate was filtered
  3. washwashed with water and ether
  4. customThe crystalline product was purified
  5. customThe crystalline product was purified

Quellen und Nachweise

ORD-Eintrag
ord-7b552c2c36364aaeaa95785705119db2
Quelldatensatz
uspto-grants-1990_09
Patentnummer
US04954507

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