Benzyl chloroformate → benzyl(3aR,6aS)-6-oxo-1,3,3a,4,5,6a-hexahydrocyclopenta[c]pyrrole-2-carboxylate

HRID 1959429Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1959429
C([N:8]1[CH2:12][C@@H:11]2[CH2:13][CH2:14][C:15](=[O:16])[C@@H:10]2[CH2:9]1)C1C=CC=CC=1.Cl[C:18]([O:20][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)=[O:19]>ClCCl>[O:16]=[C:15]1[C@@H:10]2[CH2:9][N:8]([C:18]([O:20][CH2:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)=[O:19])[CH2:12][C@@H:11]2[CH2:13][CH2:14]1

Komponenten

4

Edukt 2

HCID 10387Benzyl chloroformateHCID 25633329cis-2-Benzylhexahydrocyclopenta[c]pyrrol-4(1H)-one

Produkt 1

HCID 60006925benzyl(3aR,6aS)-6-oxo-1,3,3a,4,5,6a-hexahydrocyclopenta[c]pyrrole-2-carboxylateAusbeute 47 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A solution of (3aR,6aS)-2-benzyl-1,3,3a,4,5,6a-hexahydrocyclopenta[c]pyrrol-6-one (19.8 g, 92 mmol) in dichloromethane (770 mL) was treated with benzyl chloroformate (26.7 g, 22.3 mL, 156 mmol) at room temperature. The reaction mixture was stirred overnight at room temperature. The solvent was removed under reduced pressure and the crude material obtained was purified using silica gel column chromatography using 40 to 99% EtOAc in hexanes to obtain benzyl(3aR,6aS)-6-oxo-1,3,3a,4,5,6a-hexahydrocyclopenta[c]pyrrole-2-carboxylate (11.2 g, 43.19 mmol, 47%) as a light yellow oil. NMR (400 MHz, CDCl3) δ 7.41-7.23 (m, 5H), 5.11 (d, J=4.2 Hz, 2H), 3.82-3.52 (m, 3H), 3.29-3.14 (m, J=5.6 Hz, 1H), 3.13-2.93 (m, J=11.1, 6.8 Hz, 1H), 2.81-2.68 (m, J=8.6, 3.6 Hz, 1H), 2.37 (t, J=7.8 Hz, 2H), 2.26-2.10 (m, 1H), 1.86 (s, 1H). LC/MS m/z 260.1 [M+H]+.

Aufarbeitung

  1. customThe solvent was removed under reduced pressure
  2. customthe crude material obtained
  3. customwas purified

Quellen und Nachweise

ORD-Eintrag
ord-a2a793a4020f455c858274e0512bdb36
Quelldatensatz
uspto-grants-2013_04
Patentnummer
US08410112B2

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