Methanol → HCID 70664502, compound

HRID 1026645Notes

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]([F:23])[F: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].[F:23][CH:21]([F:22])[C:20]1[C:13]2[CH2:12][CH2:11][C@@:10]3([CH3:24])[C@H:15]([CH2:16][NH:8][CH2:9]3)[C:14]=2[CH:17]=[CH:18][CH:19]=1

Participants

Conditions

Temperature: 160 °C

Procedure

cis-2-Benzyl-6-(difluoromethyl)-3a-methyl-2,3,3a,4,5,9b-hexahydro-1H-benzo[e]isoindole (0.070 mmol, 23 mg) was dissolved in toluene (1 ml) and ACE-Cl (0.492 mmol, 0.054 ml, 70.3 mg) was added. The reaction mixture was heated to 160° C. for 15 minutes in a microwave reactor. MeOH (1 ml) was added and the reaction mixture was heated for a further 5 minutes at 160° C. in a microwave reactor and then the resulting solution was passed through an SCX cartridge. The fractions containing the desired product were concentrated in vacuo and then purified by silica column chromatography (eluting with DCM then 2-16% MeOH(NH3) in DCM) to give a crude residue that was dissolved in DCM and 2N HCl in ether (1 ml) was added. The solvent was removed in vacuo to afford cis-6-(difluoromethyl)3a-methyl-2,3,3a,4,5,9b-hexahydro-1H-benzo[e]isoindole hydrochloride (13 mg), m/z: 238.3 [M+H]+.

Workup

temperaturethe reaction mixture was heated for a further 5 minutes at 160° C. in a microwave reactor

Sources & evidence

ORD record: ord-576bedb179674f54899d652d6e2b1a75
Source dataset: uspto-grants-2014_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08729274B2

Reaction notes

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