Water → 1-{(3aS,7E,7aR)-7-(bromomethylene)-3a,4,5,6,7,7a-hexahydro-3a-methyl-1H-indene-3-yl}ethanone

HRID 1922626Notes

Reaction equation

Br[C@@:2]1([C:14](=[O:16])[CH3:15])[C@:10]2([CH3:11])[C@H:5](/[C:6](=[CH:12]/[Br:13])/[CH2:7][CH2:8][CH2:9]2)[CH2:4][CH2:3]1.[Br-].[Li+].C(=O)([O-])[O-].[Li+].[Li+].O>CN(C)C=O>[Br:13]/[CH:12]=[C:6]1\[CH2:7][CH2:8][CH2:9][C@@:10]2([CH3:11])[C@H:5]\1[CH2:4][CH:3]=[C:2]2[C:14](=[O:16])[CH3:15]

Participants

Conditions

Temperature: 100 °C

Procedure

1-{(E,1R,3aS,7aS)-1-bromo-4-(bromomethylene)-octahydro-7a-methyl-1H-indene-1-yl}ethanone (Compound 12: 100 mg, 0.369 mmol) was dissolved in dimethylformamide (1.6 ml), and lithium bromide (35.8 mg, 0.412 mmol) and lithium carbonate (27.4 mg, 0.371 mmol) were added thereto. The resulting mixture was heated to 100° C. and stirred for 3 hours. After cooling the reaction solution to room temperature, water was added thereto, and the resulting mixture was extracted with diethyl ether. The organic layer was washed with saturated brine, dried over sodium sulfate, and evaporated to obtain a crude product. The product was purified by flash column chromatography to obtain 1-{(3aS,7E,7aR)-7-(bromomethylene)-3a,4,5,6,7,7a-hexahydro-3a-methyl-1H-indene-3-yl}ethanone (71.6 mg, 94.0%) as a white solid.

Workup

temperatureAfter cooling the reaction solution to room temperature
extractionthe resulting mixture was extracted with diethyl ether
washThe organic layer was washed with saturated brine
dry with materialdried over sodium sulfate
customevaporated
customto obtain a crude product
customThe product was purified by flash column chromatography

Sources & evidence

ORD record: ord-c008845b63ed4517b566228e26c40fb7
Source dataset: uspto-grants-2012_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08173824B2

Reaction notes

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