Water → HCID 22571064, compound

HRID 1372408Notes

Reaction equation

HRID 1372408 reaction equation
[O:1]=[C:2]1[CH2:10][CH2:9][CH2:8][C:7]2[NH:6][CH:5]=[C:4]([CH:11]([CH3:15])C(O)=O)[C:3]1=2.[C:16]([N:23]1[CH:27]=[CH:26]N=[CH:24]1)(N1C=CN=C1)=[O:17].N1CCC[CH2:29]1.O>ClCCl>[O:17]=[C:16]([N:23]1[CH2:24][CH2:29][CH2:26][CH2:27]1)[CH2:15][CH2:11][C:4]1[C:3]2[C:2](=[O:1])[CH2:10][CH2:9][CH2:8][C:7]=2[NH:6][CH:5]=1

Participants

6

Reactant 4

HCID 962WaterHCID 31268PyrrolidineHCID 682631,1'-CarbonyldiimidazoleHCID 68791479HCID 68791479, compound

Product 1

HCID 22571064HCID 22571064, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of 10 g of 3-(4-oxo-4,5,6,7,tetrahydro-1H-indol-3-yl-propionic acid (48 mmol) in 60 mL of dichloromethane was added 9.3 g (57.6 mmol) of carbonyldiimidazole. After stirring at room temperature for 2 hours, 12 mL (144 mmol) of pyrrolidine was added. The dark red reaction mixture was then stirred at room temperature overnight. The reaction was poured into water and the organic layer washed with brine, dried and concentrated to give 3-(3-oxo-3-pyrrolidin-1-yl-propyl)-1,5,6,7-tetrahydro-indol-4-one (12 g, 96% yield). 1H-NMR (300 MHz, dimethylsulfoxide-d6) δ 11.05 (br s, 1H, NH), 6.46 (d, 1H), 3.35 (m, 2H, CH2), 2.24 (m, 2H, CH2), 2.66–2.73 (m, 4H, 2×CH2), 2.44 (m, 2H, CH2), 2.26 (m, 2H, CH2), 1.96 (m, 2H, CH2), 1.82 (m, 2H, CH2), 1.73 (m, 2H, CH2). MS m/z 260 [M+].

Workup

  1. customThe dark red reaction mixture
  2. stirringwas then stirred at room temperature overnight
  3. washthe organic layer washed with brine
  4. customdried
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-b69a279b5dd546ae8cc890c8bfe263b6
Source dataset
uspto-grants-2007_01
Patent number
US07157577B2

Reaction notes

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