Hydrochloric Acid → 1-{(E,3S,3aS,7aR)-7-(bromomethylene)-octahydro-3a-methyl-1H-indene-3-yl}ethanone

HRID 1922624Notes

Reaction equation

[Br:1]/[CH:2]=[C:3]1\[CH2:4][CH2:5][CH2:6][C@@:7]2([CH3:16])[C@H:11]\1[CH2:10][CH2:9][C@@H:8]2[C@H:12](C)[CH:13]=O.N1C=CC=CC=1C1C=CC=CN=1.C1N2CCN(CC2)C1.[O:37]=O.Cl>CN(C)C=O.C([O-])(=O)C.[Cu+2].C([O-])(=O)C>[Br:1]/[CH:2]=[C:3]1\[CH2:4][CH2:5][CH2:6][C@@:7]2([CH3:16])[C@H:11]\1[CH2:10][CH2:9][C@@H:8]2[C:12](=[O:37])[CH3:13]

Participants

Conditions

Temperature: 80 °C

Procedure

(S)-2-{(E,3R,3aR,7aR)-7-(bromomethylene)-octahydro-3a-methyl-1H-indene-3-yl}propanal (Compound 10: 43 mg, 0.151 mmol) synthesized according to the method described in Org. Lett. 2003, 5, 4859-4862 was dissolved in dimethylformamide (300 μl), and copper (II) acetate (3.1 mg, 0.0171 mmol), bipyridyl (2.8 mg, 0.0179 mmol) and triethylenediamine (17.4 mg, 0.155 mmol) were added thereto. The resulting mixture was heated to 80° C. and stirred for 4 hours with streaming oxygen. After cooling the mixture to room temperature, 2N hydrochloric acid was added thereto, and the resulting mixture was extracted with diethyl ether. The organic layer was washed with water and saturated brine, dried over sodium sulfate, and evaporated. The obtained product was purified by flash column chromatography to obtain 1-{(E,3S,3aS,7aR)-7-(bromomethylene)-octahydro-3a-methyl-1H-indene-3-yl}ethanone (24.1 mg, 58.8%).

Workup

temperatureAfter cooling the mixture to room temperature
extractionthe resulting mixture was extracted with diethyl ether
washThe organic layer was washed with water and saturated brine
dry with materialdried over sodium sulfate
customevaporated
customThe obtained product was purified by flash column chromatography

Sources & evidence

ORD record: ord-ecb73179bb564d97b787d3069d757127
Source dataset: uspto-grants-2012_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08173824B2

Reaction notes

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