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

HRID 1411751Notes

Reaction equation

HRID 1411751 reaction equation
[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

Participants

4

Reactant 1

HCID 600232Methyl indolizine-2-carboxylate

Product 1

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

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-196e154f69724ac398874b7d874af6b5
Source dataset
uspto-grants-2014_12
Patent number
US08921353B2

Reaction notes

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