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

HRID 1959429ノート

反応式

HRID 1959429 の反応式
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

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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]+.

後処理

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

出典と根拠

ORDレコード
ord-a2a793a4020f455c858274e0512bdb36
出典データセット
uspto-grants-2013_04
特許番号
US08410112B2

反応ノート

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