HCID 66688004, compound → HCID 66687250, compound

HRID 1895011Notes

Reaction equation

HRID 1895011 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][C:10]([CH2:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)([C:13]([C:15]2[CH:16]=[C:17]3[C:21](=[CH:22][CH:23]=2)[NH:20][C:19](=[O:24])[C:18]3(Br)Br)=[O:14])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>C(O)(=O)C.[Zn]>[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][C:10]([CH2:27][C:28]2[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=2)([C:13]([C:15]2[CH:16]=[C:17]3[C:21](=[CH:22][CH:23]=2)[NH:20][C:19](=[O:24])[CH2:18]3)=[O:14])[CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 1

HCID 66688004HCID 66688004, compound

Product 1

HCID 66687250HCID 66687250, compound

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 176Acetic AcidSolvent

Procedure

Zinc powder (130 mg, 2.00 mmol) was added to a solution of 3-benzyl-3-(3,3-dibromo-2-oxo-2,3-dihydro-1H-indole-5-carbonyl)-pyrrolidine-1-carboxylic acid tert-butyl ester (115 mg, 0.20 mmol) in acetic acid (4 mL). The reaction mixture was stirred vigorously at room temperature for 1 hour. Solids were removed by filtration, and the filtrate was concentrate under reduced pressure to give 3-benzyl-3-(2-oxo-2,3-dihydro-1H-indole-5-carbonyl)-pyrrolidine-1-carboxylic acid tert-butyl ester as a foam. The same procedure was repeated using the 3-benzyl-3-(3-bromo-2-oxo-2,3-dihydro-1H-indole-5-carbonyl)-pyrrolidine-1-carboxylic acid tert-butyl ester to provide additional 3-benzyl-3-(2-oxo-2,3-dihydro-1H-indole-5-carbonyl)-pyrrolidine-1-carboxylic acid tert-butyl ester.

Workup

  1. customSolids were removed by filtration
  2. concentrationthe filtrate was concentrate under reduced pressure

Sources & evidence

ORD record
ord-3429a96c343e4acc9250474d7bf4245a
Source dataset
uspto-grants-2013_08
Patent number
US08513425B2

Reaction notes

Loading…