Potassium Carbonate → 3-benzyl-3-(3-cyano-1H-indole-5-carbonyl)-pyrrolidine-1-carboxylic acid tert-butyl ester

HRID 1895000Notes

Reaction equation

[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][C:10]([C:20]([C:22]2[CH:23]=[C:24]3[C:28](=[CH:29][CH:30]=2)[N:27](S(C2C=CC=CC=2)(=O)=O)[CH:26]=[C:25]3[C:40]#[N:41])=[O:21])([CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+]>CO.O.[Cl-].[Na+].O>[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][C:10]([CH2:13][C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)([C:20]([C:22]2[CH:23]=[C:24]3[C:28](=[CH:29][CH:30]=2)[NH:27][CH:26]=[C:25]3[C:40]#[N:41])=[O:21])[CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

Conditions

Temperature: 50 °C

Procedure

Water (1 mL) was added to a solution of 3-(1-benzenesulfonyl-3-cyano-1H-indole-5-carbonyl)-3-benzyl-pyrrolidine-1-carboxylic acid tert-butyl ester (100 mg, 0.175 mmol) in MeOH (4 mL), followed by potassium carbonate (73 mg, 0.525 mmol). The reaction mixture was heated at 50° C. for 10 minutes, then cooled to room temperature and diluted with water and brine. The resulting mixture was extracted with DCM, dried over MgSO4, filtered and evaporated under reduced pressure. The residue was purified by flash chromatography (30% to 50% of EtOAc in hexane) to give 3-benzyl-3-(3-cyano-1H-indole-5-carbonyl)-pyrrolidine-1-carboxylic acid tert-butyl ester as white foamy solid.

Workup

temperaturecooled to room temperature
extractionThe resulting mixture was extracted with DCM
dry with materialdried over MgSO4
filtrationfiltered
customevaporated under reduced pressure
customThe residue was purified by flash chromatography (30% to 50% of EtOAc in hexane)

Sources & evidence

ORD record: ord-41f60a3d64d94360899a00256639715d
Source dataset: uspto-grants-2013_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08513425B2

Reaction notes

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