Potassium Carbonate → N-Ethylcarbamate 5-cyclopropylmethoxy-8-methyl-1,2,3,3a,8,8a-hexahydroindeno[1,2-c]pyrrole

HRID 508526Notes

Reaction equation

Br[CH2:2][CH:3]1[CH2:5][CH2:4]1.C([O-])([O-])=O.[K+].[K+].[CH2:12]([NH:14][C:15](=[O:17])[O-:16])[CH3:13].[OH:18][C:19]1[CH:20]=[CH:21][C:22]2[CH:23]([CH3:31])[CH:24]3[CH2:28][NH:27][CH2:26][CH:25]3[C:29]=2[CH:30]=1>CC#N.O.C(Cl)Cl>[CH2:12]([NH:14][C:15](=[O:16])[O-:17])[CH3:13].[CH:5]1([CH2:4][O:18][C:19]2[CH:20]=[CH:21][C:22]3[CH:23]([CH3:31])[CH:24]4[CH2:28][NH:27][CH2:26][CH:25]4[C:29]=3[CH:30]=2)[CH2:3][CH2:2]1

Participants

Conditions

Temperature: 80 °C

Procedure

(Bromomethyl)cyclopropane (13 mg, 0.09 mmol) and K2CO3 (24 mg, 0.17 mmol) were added to a solution of N-ethylcarbamate-5-hydroxy-8-methyl-1,2,3,3a,8,8a-hexahydroindeno[1,2-c]pyrrole (23 mg, 0.09 mmol) in CH3CN, and stirred overnight at 80° C. The reaction mixture was diluted with H2O and CH2Cl2, and filtered through an Extrelut column. The column was washed with CH2Cl2, and the filtrate was concentrated. The subtitle compound was obtained without further purification. MS calculated for C19H25NO3+H: 316, observed: 316.

Workup

filtrationfiltered through an Extrelut column
washThe column was washed with CH2Cl2
concentrationthe filtrate was concentrated

Sources & evidence

ORD record: ord-48c9ac9e963d4509a6476aa33a6ca4ab
Source dataset: uspto-grants-2015_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09096520B2

Reaction notes

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