Ethyl formate → trans-3-(3-Cyclopentoxy-4-methoxyphenyl)-1-formyl-4-(methoxycarbonyl)pyrrolidine

HRID 1377767노트

반응식

HRID 1377767 반응식
[CH:1]1([O:6][C:7]2[CH:8]=[C:9]([C@H:15]3[C@H:19]([C:20]([O:22][CH3:23])=[O:21])[CH2:18][NH:17][CH2:16]3)[CH:10]=[CH:11][C:12]=2[O:13][CH3:14])[CH2:5][CH2:4][CH2:3][CH2:2]1.[CH:24](OCC)=[O:25]>CCOCC>[CH:1]1([O:6][C:7]2[CH:8]=[C:9]([C@H:15]3[C@H:19]([C:20]([O:22][CH3:23])=[O:21])[CH2:18][N:17]([CH:24]=[O:25])[CH2:16]3)[CH:10]=[CH:11][C:12]=2[O:13][CH3:14])[CH2:2][CH2:3][CH2:4][CH2:5]1

참가 물질

4

반응물 2

HCID 8025Ethyl formateHCID 70093357trans-3-(3-Cyclopentoxy-4-methoxyphenyl)-4-(methoxycarbonyl)pyrrolidine

생성물 1

HCID 44302662trans-3-(3-Cyclopentoxy-4-methoxyphenyl)-1-formyl-4-(methoxycarbonyl)pyrrolidine수율 84%

시약·촉매·용매 1

HCID 3283Diethyl Ether용매

실험 절차

A solution of trans-3-(3-cyclopentoxy-4-methoxyphenyl)-4-(methoxycarbonyl)pyrrolidine (620 mg, 1.94 mmol) in 5 mL of ethyl formate was heated at reflux for 3 hr. The reaction was diluted with ether and concentrated. The residue was dissolved in ether and washed with 1M H3PO4. The organic layer was dried over MgSO4, filtered, and concentrated under reduced pressure. Silica gel chromatography (2:1, ethyl acetate:hexanes) provided trans-3-(3-cyclopentoxy-4-methoxyphenyl)-1-formyl-4-(methoxycarbonyl)pyrrolidine as a colorless oil (567 mg, 84%). 1H-NMR (300 MHz): δ 3.11-3.21 (1, m), 3.65 (s, 3), 3.82 (s, 3), 6.73-6.82 (m, 3), 8.26 (s, 1).

후처리

  1. temperatureat reflux for 3 hr
  2. concentrationconcentrated
  3. dissolutionThe residue was dissolved in ether
  4. washwashed with 1M H3PO4
  5. dry with materialThe organic layer was dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-905613e565ec450987de5197bac8bb70
출처 데이터셋
uspto-grants-1997_09
특허 번호
US05665754

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