Pyrrolidine → HCID 68858354, compound

HRID 2102736Notes

Reaction equation

HRID 2102736 reaction equation
[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][C:7](=[O:11])[NH:8]2)=[CH:4][CH:3]=1.[C:12]([O:16][C:17](=[O:27])[N:18]([CH2:22][CH2:23][C:24](=O)[CH3:25])[CH2:19][CH2:20]C)([CH3:15])([CH3:14])[CH3:13].N1CCCC1>CC(O)C>[C:12]([O:16][C:17]([N:18]1[CH2:19][CH2:20][CH2:25][C:24](=[C:6]2[C:5]3[C:9](=[CH:10][C:2]([Cl:1])=[CH:3][CH:4]=3)[NH:8][C:7]2=[O:11])[CH2:23][CH2:22]1)=[O:27])([CH3:13])([CH3:14])[CH3:15]

Participants

5

Reactant 3

HCID 31268PyrrolidineHCID 7363446-Chloro-1,3-dihydroindol-2-oneHCID 86609724HCID 86609724, compound

Product 1

HCID 68858354HCID 68858354, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
90 °C

Procedure

A suspension of 6-chlorooxindole (0.71 g, 4.24 mmol) (Cresent Chem.), (3-oxo-butyl)-propyl-carbamic acid tert-butyl ester (1 g, 4.69 mmol) (Tyger Sci.), and pyrrolidine (0.1 g) (Aldrich) in 2-propanol (15 mL) was heated at 90° C. for 2 days. The mixture was allowed to cool to room temperature. The solvent was removed and the residue was purified by chromatography to give 4-(6-chloro-2-oxo-1,2-dihydro-indol-3-ylidene)-azepane-1-carboxylic acid tert-butyl ester as a brown solid. (Yield: 1.36 g, 88%).

Workup

  1. temperatureto cool to room temperature
  2. customThe solvent was removed
  3. customthe residue was purified by chromatography

Sources & evidence

ORD record
ord-057b47a9ac0246c69b0bb452f386d147
Source dataset
uspto-grants-2009_08
Patent number
US07576082B2

Reaction notes

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