Ethyl Acetate → HCID 70664691, compound

HRID 1026650Notes

Reaction equation

[CH2:1]([N:8]1[CH2:16][C@@H:15]2[C@:10]([CH3:23])([CH2:11][CH2:12][C:13]3[C:20]([Cl:21])=[C:19](Br)[CH:18]=[CH:17][C:14]=32)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C[O-].[Na+].[C:27](OCC)(=[O:29])C>CO.[Cu]Br>[CH2:1]([N:8]1[CH2:16][C@@H:15]2[C@:10]([CH3:23])([CH2:11][CH2:12][C:13]3[C:20]([Cl:21])=[C:19]([O:29][CH3:27])[CH:18]=[CH:17][C:14]=32)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 120 °C

Procedure

A mixture of trans-2-benzyl-7-bromo-6-chloro-3a-methyl-2,3,3a,4,5,9b-hexahydro-1H-benzo[e]isoindole (0.704 mmol, 275 mg), sodium methoxide (8.75 mmol, 2 ml, 1890 mg), copper(I) bromide (0.352 mmol, 51.5 mg) and ethyl acetate (0.699 mmol, 69 μl, 62.2 mg) in MeOH (2 ml) was heated in a microwave reactor at 120° C. for 0.5 h. The reaction mixture was partitioned between DCM and water and the aqueous was further extracted with DCM. The combined organic extracts were dried over Na2SO4 and concentrated in vacuo before being purified by silica column chromatography (eluting with neat DCM—5% MeOH in DCM) to afford the trans-2-benzyl-6-chloro-7-methoxy-3a-methyl-2,3,3a,4,5,9b-hexahydro-1H-benzo[e]isoindole (26.4 mg), m/z=342.2, 344.2 [M+H]+.

Workup

customThe reaction mixture was partitioned between DCM and water
extractionthe aqueous was further extracted with DCM
dry with materialThe combined organic extracts were dried over Na2SO4
concentrationconcentrated in vacuo
custombefore being purified by silica column chromatography (eluting with neat DCM—5% MeOH in DCM)

Sources & evidence

ORD record: ord-7ae2dca72a0c4078b1858e060ce73f6e
Source dataset: uspto-grants-2014_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08729274B2

Reaction notes

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