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Water → (2R,4R)-tert-butyl 2-methyl-4-(tosyloxy)pyrrolidine-1-carboxylate

HRID 13777
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 13777
[C:1]([O:5][C:6]([N:8]1[CH2:12][C@H:11]([OH:13])[CH2:10][C@H:9]1[CH3:14])=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:15]1([CH3:25])[CH:20]=[CH:19][C:18]([S:21](Cl)(=[O:23])=[O:22])=[CH:17][CH:16]=1.O>ClCCl.C(N(CC)CC)C>[C:1]([O:5][C:6]([N:8]1[CH2:12][C@H:11]([O:13][S:21]([C:18]2[CH:19]=[CH:20][C:15]([CH3:25])=[CH:16][CH:17]=2)(=[O:23])=[O:22])[CH2:10][C@H:9]1[CH3:14])=[O:7])([CH3:4])([CH3:2])[CH3:3]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 3

HCID 962WaterHCID 73974-Toluenesulfonyl chlorideHCID 14117010tert-butyl (2R,4R)-4-hydroxy-2-methylpyrrolidine-1-carboxylate

Produkt 1

HCID 86612723(2R,4R)-tert-butyl 2-methyl-4-(tosyloxy)pyrrolidine-1-carboxylateAusbeute 85,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittel
HCID 8471TriethylamineLösungsmittel

Versuchsvorschrift

To a solution of 1.02 g of (2R,4R)-1-(t-butoxycarbonyl)-4-hydroxy-2-methylpyrrolidine (J. Med. Chem., 1988, 31, 1598-1611) in 10 ml of anhydrous dichloromethane, 1.7 ml of triethylamine and 1.16 g of p-toluenesulfonyl chloride were added, and then the mixture was stirred at room temperature overnight. The reaction solution was mixed with water, and followed by extraction with ethyl acetate twice. The organic layers were combined, washed in turn with water, 1N hydrochloric acid and a 1N aqueous sodium hydroxide solution and dried over anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography to obtain 1.54 g of the objective compound as a colorless oily product.

Aufarbeitung

  1. extractionfollowed by extraction with ethyl acetate twice
  2. washwashed in turn with water, 1N hydrochloric acid
  3. dry with materiala 1N aqueous sodium hydroxide solution and dried over anhydrous sodium sulfate
  4. distillationthe solvent was distilled off under reduced pressure
  5. customThe residue was purified by silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-7dea641aca3c49829f4b05f3cf36b2e6
Quelldatensatz
uspto-grants-2010_06
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07728131B2

Notizen zur Reaktion

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