Acetic Acid → N-Ethylcarbamate 5-methoxy-6-chloro-8-methyl-1,2,3,3a,8,8a-hexahydroindeno[1,2-c]pyrrole

HRID 508496Notes

Reaction equation

[Cl:1]N1C(=O)CCC1=O.C(O)(=O)C.[CH2:13]([NH:15][C:16](=[O:18])[O-:17])[CH3:14].[CH3:19][O:20][C:21]1[CH:22]=[CH:23][C:24]2[CH:25]([CH3:33])[CH:26]3[CH2:30][NH:29][CH2:28][CH:27]3[C:31]=2[CH:32]=1>ClCCCl.C(Cl)Cl>[CH2:13]([NH:15][C:16](=[O:17])[O-:18])[CH3:14].[CH3:19][O:20][C:21]1[C:22]([Cl:1])=[CH:23][C:24]2[CH:25]([CH3:33])[CH:26]3[CH2:30][NH:29][CH2:28][CH:27]3[C:31]=2[CH:32]=1

Participants

Conditions

Temperature: 60 °C

Procedure

N-chlorosuccinimide (0.22 g, 1.6 mmol) and acetic acid (8 mL) were added to a solution of N-ethylcarbamate-5-methoxy-8-methyl-1,2,3,3a,8,8a-hexahydroindeno[1,2-c]pyrrole (from Example 2, Step A) (0.45 g, 1.6 mmol) in DCE (8 mL), and stirred for 3 hours at 60° C. The reaction mixture was cooled to room temperature, diluted with CH2Cl2 (50 mL), and washed with H2O (50 mL). The organic extract was dried over MgSO4 and concentrated. The crude product was purified by column chromatography (SiO2) using a 0-35% ethyl acetate-hexanes gradient to afford 250 mg (51%) of the subtitle compound. MS calculated for C16H20ClNO3+H: 310, observed: 310.

Workup

temperatureThe reaction mixture was cooled to room temperature
washwashed with H2O (50 mL)
extractionThe organic extract
dry with materialwas dried over MgSO4
concentrationconcentrated
customThe crude product was purified by column chromatography (SiO2)

Sources & evidence

ORD record: ord-6cedec53c5d84a5d962c4091cf3e96fd
Source dataset: uspto-grants-2015_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09096520B2

Reaction notes

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