Methanesulfonic Acid → HCID 89669847, compound

HRID 1775242Notes

Reaction equation

CO[C:3](=[O:24])[CH2:4][N:5]1[CH2:9][CH2:8][CH2:7][C@@:6]1([C:11]1[NH:12][C:13]2[CH:14]=[CH:15][CH:16]=[C:17]([C:20]([O:22][CH3:23])=[O:21])[C:18]=2[CH:19]=1)[CH3:10].CS(O)(=O)=O.C([O-])(O)=O.[Na+]>O>[CH3:10][C@@:6]12[C:11]3[NH:12][C:13]4[CH:14]=[CH:15][CH:16]=[C:17]([C:20]([O:22][CH3:23])=[O:21])[C:18]=4[C:19]=3[C:3](=[O:24])[CH2:4][N:5]1[CH2:9][CH2:8][CH2:7]2

Participants

Conditions

Temperature: 60 °C

Procedure

In a 25-mL flask, (R)-methyl 2-(1-(2-methoxy-2-oxoethyl)-2-methylpyrrolidin-2-yl)-1H-indole-4-carboxylate (146 mg, 0.44 mmol) was treated with anhydrous MeSO3H (10 mL). The flask was fitted with a reflux condenser and heated to 60° C. for 1 h. Then, the reaction mixture was cooled in an ice-bath and diluted with distilled water (2.0 mL). The pH of the solution was increased to pH-10 by the addition of saturated aq. NaHCO3. The reaction mixture was then extracted with EtOAc (3×20 mL), and the organic extracts were washed with brine (1×20 mL), dried over Na2SO4, filtered, and concentrated. The residue was purified by flash chromatography (20 to 60% EtOAc/hexanes) to give (R)-methyl 11b-methyl-6-oxo-2,3,5,6,11,11b-hexahydro-1H-indolizino[8,7-b]indole-7-carboxylate (58 mg 44%). MS (ESI) m/e [M+1]+ 299.0.

Workup

customThe flask was fitted with a reflux condenser
temperatureThen, the reaction mixture was cooled in an ice-bath
extractionThe reaction mixture was then extracted with EtOAc (3×20 mL)
washthe organic extracts were washed with brine (1×20 mL)
dry with materialdried over Na2SO4
filtrationfiltered
concentrationconcentrated
customThe residue was purified by flash chromatography (20 to 60% EtOAc/hexanes)

Sources & evidence

ORD record: ord-1df7035db2bc4af99590e843ac555749
Source dataset: uspto-grants-2016_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09260440B2

Reaction notes

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