Pyrrolidine → (S)-7-(1-Pyrrolidinyl)-1,2,3,5,8,8a-hexahydroindolizin-5-one

HRID 9889Notes

Reaction equation

HRID 9889 reaction equation
[CH2:1]1[C@@H:9]2[N:4]([C:5](=[O:11])[CH2:6][C:7](=O)[CH2:8]2)[CH2:3][CH2:2]1.[NH:12]1[CH2:16][CH2:15][CH2:14][CH2:13]1>C(O)C>[NH:4]1[CH2:9][CH2:1][CH2:2][CH2:3]1.[N:12]1([C:7]2[CH2:8][C@H:9]3[N:4]([CH2:3][CH2:2][CH2:1]3)[C:5](=[O:11])[CH:6]=2)[CH2:16][CH2:15][CH2:14][CH2:13]1

Participants

5

Reactant 2

HCID 31268PyrrolidineHCID 58681494HCID 58681494, compound

Product 2

HCID 31268PyrrolidineHCID 58681493(S)-7-(1-Pyrrolidinyl)-1,2,3,5,8,8a-hexahydroindolizin-5-oneYield 204.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

(S)-1,2,3,5,6,7,8,8a-octahydroindolizin-5,7-dione (117 mg (0.76 mmol), prepared as described in 3)) was dissolved in ethanol (1.2 ml). To the solution was added pyrrolidine (128 μl, 1.53 mmol), and the resulting mixture was allowed to stand at room temperature for 5 minutes. At the end of this time, the reaction mixture was concentrated by distillation under reduced pressure to remove solvents and any excess of pyrrolidine, to give the title compound (160 mg) as a light yellow powder (yield quantitative).

Workup

  1. concentrationAt the end of this time, the reaction mixture was concentrated by distillation under reduced pressure
  2. customto remove solvents

Sources & evidence

ORD record
ord-5f9f9d01fa924902888dbe11994c4910
Source dataset
uspto-grants-2006_08
Patent number
US07091352B2

Reaction notes

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