Methyl indolizine-2-carboxylate → Methyl 5,6,7,8-Tetrahydroindolizine-2-carboxylate

HRID 592814노트

반응식

HRID 592814 반응식
[CH:1]1[C:2]([C:10]([O:12][CH3:13])=[O:11])=[CH:3][N:4]2[C:9]=1[CH:8]=[CH:7][CH:6]=[CH:5]2>[Pd].CO>[CH:1]1[C:2]([C:10]([O:12][CH3:13])=[O:11])=[CH:3][N:4]2[C:9]=1[CH2:8][CH2:7][CH2:6][CH2:5]2

참가 물질

4

반응물 1

HCID 600232Methyl indolizine-2-carboxylate

생성물 1

HCID 13115072Methyl 5,6,7,8-Tetrahydroindolizine-2-carboxylate수율 81%

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 887Methanol용매

실험 절차

A 250-mL round-bottomed flask was purged with nitrogen and charged with 193b (2.0 g, 11.4 mmol), 10% palladium on carbon (50% wet, 200 mg), and methanol (50 mL). It was evacuated, charged with hydrogen gas, and stirred under 5 atm hydrogen at room temperature for 8 h. The hydrogen was then evacuated and nitrogen was charged into the flask. The catalyst was removed by filtration through a pad of CELITE® and the filtrate concentrated under reduced pressure to afford 193c as a white solid (1.1 g, 81%). MS-ESI: [M+H]+ 180.3. 1H NMR (500 MHz, DMSO-d6) δ 7.25 (d, J=2.0 Hz, 1H), 6.09 (s, 1H), 3.93 (t, J=6.0 Hz, 2H), 3.66 (s, 3H), 2.67 (t, J=6.0 Hz, 2H), 1.87-1.83 (m, 2H), 1.75-1.70 (m, 2H).

후처리

  1. customA 250-mL round-bottomed flask was purged with nitrogen
  2. customIt was evacuated
  3. additioncharged with hydrogen gas
  4. customThe hydrogen was then evacuated
  5. additionnitrogen was charged into the flask
  6. customThe catalyst was removed by filtration through a pad of CELITE®
  7. concentrationthe filtrate concentrated under reduced pressure

출처 및 근거

ORD 기록
ord-a2d668ed6a79498598fcf161cead3541
출처 데이터셋
uspto-grants-2016_01
특허 번호
US09238655B2

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