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

HRID 1026635Notes

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]([C:21]([CH3:23])=[CH2:22])=[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]([C:21]([CH3:23])=[CH2:22])[C:13]=1[CH2:12][CH2:11]2

Participants

Conditions

Temperature: 160 °C

Procedure

trans-2-Benzyl-3a-methyl-6-(prop-1-en-2-yl)-2,3,3a,4,5,9b-hexahydro-1H-benzo[e]isoindole (0.359 mmol, 134 mg) was dissolved in toluene (1 ml). ACE-Cl (2.95 mmol, 325 μl) was added and the reaction mixture was heated in a microwave reactor at 160° C. for 15 minutes. MeOH (1 ml) was added and the mixture was again heated in a microwave reactor at 160° C. for 5 minutes. The resulting mixture was passed through an SCX cartridge and the resulting filtrate was concentrated in vacuo to give a crude residue that was purified by preparative-HPLC. To the pure fractions was added HCl in ether (1 ml) and the resulting solution was concentrated in vacuo to afford trans-3a-methyl-6-(prop-1-en-2-yl)-2,3,3a,4,5,9b-hexahydro-1H-benzo[e]isoindole hydrochloride (41 mg), MS m/z: 228.1 [M+H]+.

Workup

temperaturethe mixture was again heated in a microwave reactor at 160° C. for 5 minutes
concentrationthe resulting filtrate was concentrated in vacuo
customto give a crude residue that
customwas purified by preparative-HPLC
additionTo the pure fractions was added HCl in ether (1 ml)
concentrationthe resulting solution was concentrated in vacuo

Sources & evidence

ORD record: ord-4a9369a1e4b44f738f07e18a81196bd2
Source dataset: uspto-grants-2014_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08729274B2

Reaction notes

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