Sodium Carbonate → trans-2-benzyl-3a-methyl-6-((Z)-prop-1-enyl)-2,3,3a,4,5,9b-hexahydro-1H-benzo[e]isoindole

HRID 1026636Notes

Reaction equation

[CH2:1]([N:8]1[CH2:16][C@@H:15]2[C@:10]([CH3:22])([CH2:11][CH2:12][C:13]3[C:20](Br)=[CH:19][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)([O-])[O-].[Na+].[Na+].[CH:29](/B(O)O)=[CH:30]/[CH3:31]>COCCOC.C(O)C.O>[CH2:1]([N:8]1[CH2:16][C@@H:15]2[C@:10]([CH3:22])([CH2:11][CH2:12][C:13]3[C:20](/[CH:29]=[CH:30]\[CH3:31])=[CH:19][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: 160 °C

Procedure

trans-2-Benzyl-6-bromo-3a-methyl-2,3,3a,4,5,9b-hexahydro-1H-benzo[e]isoindole (0.561 mmol, 200 mg) was dissolved in DME (1 ml) and ethanol (0.5 ml). 2 N sodium carbonate solution (1 ml) was added along with (Z)-prop-1-enylboronic acid (0.842 mmol, 72.3 mg) and tetrakis(triphenylphosphine)Pd(0) (0.028 mmol, 32.4 mg). The reaction mixture was heated to 160° C. for 15 minutes in a microwave reactor and then diluted with water. The resulting mixture was extracted with DCM (3×) and the combined organic extracts were dried over Na2SO4 and concentrated in vacuo to afford a crude residue that was purified by silica column chromatography (eluting with 10% EtOAc in heptane) to afford trans-2-benzyl-3a-methyl-6-((Z)-prop-1-enyl)-2,3,3a,4,5,9b-hexahydro-1H-benzo[e]isoindole (120 mg), m/z: 318.2 [M+H]+.

Workup

extractionThe resulting mixture was extracted with DCM (3×)
dry with materialthe combined organic extracts were dried over Na2SO4
concentrationconcentrated in vacuo
customto afford a crude residue that
customwas purified by silica column chromatography (eluting with 10% EtOAc in heptane)

Sources & evidence

ORD record: ord-11fb4c9a2022406b955fdd9dfca223af
Source dataset: uspto-grants-2014_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08729274B2

Reaction notes

Loading…