4-Toluenesulfonyl chloride → 3-Tosyl-Cbz-(R)-Pyrrolidine

HRID 50134Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 50134
O[C@@H:2]1[CH2:6][CH2:5][N:4]([C:7]([O:9][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[O:8])[CH2:3]1.[C:17]1([CH3:27])[CH:22]=[CH:21][C:20]([S:23](Cl)(=[O:25])=[O:24])=[CH:19][CH:18]=1.C(N(CC)CC)C>C(Cl)Cl>[S:23]([C@@H:2]1[CH2:6][CH2:5][N:4]([C:7]([O:9][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[O:8])[CH2:3]1)([C:20]1[CH:21]=[CH:22][C:17]([CH3:27])=[CH:18][CH:19]=1)(=[O:25])=[O:24]

Komponenten

5

Edukt 3

HCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 11183628(R)-(-)-1-CBZ-3-pyrrolidinol

Produkt 1

HCID 671827093-Tosyl-Cbz-(R)-PyrrolidineAusbeute 94,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

3-Hydroxy-Cbz-(R)-pyrrolidine (13.7 g, 0.06 mol) was dissolved in CH2Cl2 (250 mL) and cooled to 0° C. p-Toluenesulfonyl chloride (14.16 g, 0.07 mol), and triethylamine (20.7 mL, 0.15 mol) were added and the resulting solution was stirred for 4 h at 0° C. The solution was washed with 1 M HCl, saturated NaHCO3, and brine. The organic solution was dried over MgSO4 and concentrated. The crude product was purified by column chromatography eluting with ethyl acetate/hexanes (3/1, v/v) to afford 20.4 g (88% yield) of the desired product as an oil.

Aufarbeitung

  1. additionwere added
  2. washThe solution was washed with 1 M HCl, saturated NaHCO3, and brine
  3. dry with materialThe organic solution was dried over MgSO4
  4. concentrationconcentrated
  5. customThe crude product was purified by column chromatography
  6. washeluting with ethyl acetate/hexanes (3/1

Quellen und Nachweise

ORD-Eintrag
ord-07474fe0098e46b69ab3174fed49cc66
Quelldatensatz
uspto-grants-2004_03
Patentnummer
US06710186B2

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