Reaction equation
[Br:1][CH:2]=[C:3]1[CH2:11][CH2:10][CH2:9][C@@:8]2([CH3:12])[CH:4]1[CH2:5][CH2:6][C@@H:7]2[C@H:13]([CH3:17])[CH2:14][C:15]#N.ClCCl.S([O-])([O-])(=O)=[O:22].[Na+].[Na+].Cl>C(OCC)(=O)C.CO.C1(C)C=CC=CC=1>[Br:1][CH:2]=[C:3]1[CH2:11][CH2:10][CH2:9][C@@:8]2([CH3:12])[CH:4]1[CH2:5][CH2:6][C@@H:7]2[C@H:13]([CH3:17])[CH2:14][CH2:15][OH:22]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 3
Conditions
- Temperature
- -70 °C
Procedure
A 84 mg amount of (3R)-3-[(1R,7aR)-octahydro-4-bromomethylene-7a-methyl-1H-inden-1-yl]butyronitrile was taken in a 25 ml eggplant-shaped flask, then 5 ml of dried dichloromethane was then added to dissolve the same. The solution was cooled by a -70° C. bath, then 660 μl of a 1.5 M [(CH3)2CHCH2 ]2AlH/toluene solution was added dropwise. The solution was stirred at the same temperature for 1 hour, then 0.5 ml of a saturated aqueous solution of sodium sulfate, 0.3 ml of methanol, 0.5 ml of 2 N hydrochloric acid, and 15 ml of ethyl acetate were added and the solution stirred for 30 minutes. The reaction solution was filtered by Celite, then was washed by a saturated solution of ammonium chloride and saturated saline, then was dried over anhydrous magnesium sulfate and the desiccant filtered out. The solvent was distilled off under reduced pressure to obtain (3R)-3-[(1R,7aR)-octahydro-4-bromomethylene-7a-methyl-1H-inden-1-yl]butanol in an amount of 85 mg.
Workup
- dissolutionto dissolve the same
- stirringthe solution stirred for 30 minutes
- filtrationThe reaction solution was filtered by Celite
- washwas washed by a saturated solution of ammonium chloride and saturated saline
- dry with materialwas dried over anhydrous magnesium sulfate
- filtrationthe desiccant filtered out
- distillationThe solvent was distilled off under reduced pressure
Sources & evidence
- ORD record
- ord-bb88a666f16e42b68a3d81f342cf18c2
- Source dataset
- uspto-grants-1998_02
- Patent number
- US05719297
Linked notes
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