Methanol → cis-3a-Methyl-6-((Z)-prop-1-enyl)-2,3,3a,4,5,9b-hexahydro-1H-benzo[e]isoindole hydrochloride

HRID 1026630Notes

Reaction equation

C([N:8]1[CH2:16][C@H:15]2[C@:10]([CH3:24])([CH2:11][CH2:12][C:13]3[C:20](/[CH:21]=[CH:22]\[CH3:23])=[CH:19][CH:18]=[CH:17][C:14]=32)[CH2:9]1)C1C=CC=CC=1.CC(Cl)OC([Cl:30])=O.CO>C1(C)C=CC=CC=1>[ClH:30].[CH3:24][C@@:10]12[CH2:9][NH:8][CH2:16][C@@H:15]1[C:14]1[CH:17]=[CH:18][CH:19]=[C:20](/[CH:21]=[CH:22]\[CH3:23])[C:13]=1[CH2:12][CH2:11]2

Participants

Conditions

Temperature: 160 °C

Procedure

cis-2-Benzyl-3a-methyl-6-((Z)-prop-1-enyl)-2,3,3a,4,5,9b-hexahydro-1H-benzo[e]isoindole (0.372 mmol, 118 mg) was dissolved in toluene (1 ml) and ACE-Cl (2.60 mmol, 0.286 ml, 372 mg) was added. The reaction mixture was heated to 160° C. for 15 minutes and then MeOH (1 ml) was added and the reaction mixture was heated to 160° C. for a further 5 minutes and then passed through an SCX cartridge and the resulting filtrate was purified by silica column chromatography (eluting with DCM—2, 4, 8, 16% MeOH(NH3)/DCM) The pure fractions were concentrated in vacuo and then 2 N HCl in MeOH added. The resulting solution was concentrated in vacuo to afford cis-3a-methyl-6-((Z)-prop-1-enyl)-2,3,3a,4,5,9b-hexahydro-1H-benzo[e]isoindole hydrochloride (85 mg): m/z: 228.1 [M+H]+.

Workup

temperaturethe reaction mixture was heated to 160° C. for a further 5 minutes
customthe resulting filtrate was purified by silica column chromatography (eluting with DCM—2, 4, 8, 16% MeOH(NH3)/DCM) The pure fractions
concentrationwere concentrated in vacuo
addition2 N HCl in MeOH added
concentrationThe resulting solution was concentrated in vacuo

Sources & evidence

ORD record: ord-37a87d547ecd4bd492495726760eb2db
Source dataset: uspto-grants-2014_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08729274B2

Reaction notes

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