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

HRID 1959429노트

반응식

HRID 1959429 반응식
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

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

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]+.

후처리

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

출처 및 근거

ORD 기록
ord-a2a793a4020f455c858274e0512bdb36
출처 데이터셋
uspto-grants-2013_04
특허 번호
US08410112B2

반응 노트

불러오는 중…