Pyrrolidine → Tert-butyl pyrrolidin-1-ylsulfonylcarbamate

HRID 1893091Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1893091
[C:1]([O:5][C:6]([N-:8][S:9]([N:12]1[CH:17]=[CH:16][C:15](=[N+](C)C)[CH:14]=C1)(=[O:11])=[O:10])=[O:7])([CH3:4])([CH3:3])[CH3:2].N1CCCC1>C(Cl)Cl>[C:1]([O:5][C:6]([NH:8][S:9]([N:12]1[CH2:17][CH2:16][CH2:15][CH2:14]1)(=[O:10])=[O:11])=[O:7])([CH3:2])([CH3:3])[CH3:4]

Komponenten

4

Edukt 2

HCID 31268PyrrolidineHCID 178482962HCID 178482962, Verbindung

Produkt 1

HCID 58765259Tert-butyl pyrrolidin-1-ylsulfonylcarbamate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A suspension of N-(tert-butoxycarbonyl)-N-[4-(dimethylazaniumylidene)-1,4-dihydropyridin-1-ylsulfonyl]azanide (3 g; 9.955 mmol) prepared according to the procedure from Winum et al (Organic Letters 2001, 3, 2241) in DCM (24 mL) was treated with pyrrolidine (0.864 mL; 10.453 mmol) and stirred at rt for 24 h. The reaction mixture was chromatographed by FC on silica gel (eluent: CH2Cl2/EtOAc 100:1) to give [N-(tert-butoxycarbonyl)]-pyrrolidine-1-sulfonic acid amide. TLC: Rf (DCM/EtOAc 100:1)=0.40. A solution of [N-(tert-butoxycarbonyl)]-pyrrolidine-1-sulfonic acid amide (57.09 g; 223 mmol) in DCM (450 mL) was treated with TFA (120 mL; 1.56 mol) and stirred at rt for 7 h. The reaction mixture was concentrated in vacuo and the residual oil was triturated with diisopropylether. The resulting powder was washed with diisopropylether and dried under high vacuum to provide Compound 1a. TLC: Rf (DCM/EtOAc 50:1)=0.10.

Aufarbeitung

  1. customprepared
  2. customThe reaction mixture was chromatographed by FC on silica gel (eluent: CH2Cl2/EtOAc 100:1)

Quellen und Nachweise

ORD-Eintrag
ord-5842c914729f4f51a14d5d2acdda3ce5
Quelldatensatz
uspto-grants-2013_08
Patentnummer
US08512690B2

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