Triethylamine → 1-[({[(1R,2R)-2-(pent-4-yn-1-yl)cyclopropyl]oxy}carbonyl)oxy]pyrrolidine-2,5-dione

HRID 522357

Reaktionsgleichung

Reaktionsgleichung von HRID 522357
[CH2:1]([C@@H:6]1[CH2:8][C@H:7]1[OH:9])[CH2:2][CH2:3][CH:4]=[CH2:5].[CH2:10]1[C:15](=[O:16])[N:14]([O:17][C:18](ON2C(=O)CCC2=O)=[O:19])[C:12](=[O:13])[CH2:11]1.C(N(CC)CC)C>C(#N)C>[CH2:1]([C@@H:6]1[CH2:8][C@H:7]1[O:9][C:18]([O:17][N:14]1[C:15](=[O:16])[CH2:10][CH2:11][C:12]1=[O:13])=[O:19])[CH2:2][CH2:3][C:4]#[CH:5]

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 676246Di(succinimido) carbonateHCID 67304189rel-(1R,2R)-2-(pent-4-en-1-yl)cyclopropan-1-ol

Produkt 1

HCID 895908351-[({[(1R,2R)-2-(pent-4-yn-1-yl)cyclopropyl]oxy}carbonyl)oxy]pyrrolidine-2,5-dione

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

To a solution of (1R,2R)-2-(pent-4-en-1-yl)cyclopropanol (see International Patent Application Publication No. WO 08/057209) (17.1 g) in acetonitrile (193 mL) was added N,N′-disuccinimidyl carbonate (49.3 g) then triethylamine (53.7 mL) The mixture was heated to 40° C. for 18 hours. The reaction mixture was cooled to room temperature and the solids were removed by filtration. The solvent was removed in vacuo. The residue was purified by flash chromatography (ISCO, 10 to 70% ethyl acetate in hexanes) to give the desired product (18 g). 1H NMR (500 MHz, CDCl3): δ (ppm) 4.06-4.03 (m, 1H), 2.87 (s, 4H), 2.28-2.25 (m, 2H), 1.98-1.97 (m, 1H), 1.72-1.63 (m, 2H), 1.44-1.39 (m, 2H), 1.30-1.25 (m, 1H), 1.12-1.08 (m, 1H), 0.72-0.68 (m, 1H).

Aufarbeitung

  1. customthe solids were removed by filtration
  2. customThe solvent was removed in vacuo
  3. customThe residue was purified by flash chromatography (ISCO, 10 to 70% ethyl acetate in hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-2fbb07a12b844ce7b8c488083552361b
Quelldatensatz
uspto-grants-2016_05
Patentnummer
US09328138B2

Verknüpfte Notizen

Wird geladen…