octahydro-4,7-methano-1H-inden-5-ol

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: With stirring, 1.7 g of diethyl azodicarboxylate, diluted with 5 ml of THF, were added to a solution of 1.66 g of octahydro-4,7-methanoinden-5-ol, 1.47 g of phthalimide, and 2.62 g of triphenylphosphine in 15 ml of THF. The reaction mixture was allowed to stand overnight and then concentrated, the residue was stirred with ether, the precipitate was filtered off with suction, and the filtrate was concentrated. The residue was purified over silica gel using toluene. This gave 1.36 g of a yellow oil. concentrated the residue was stirred with ether the precipitate was filtered off with suction the filtrate was concentrated The residue was purified over silica gel

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: With stirring, 1.7 g of diethyl azodicarboxylate, diluted with 5 ml of THF, were added to a solution of 1.66 g of octahydro-4,7-methanoinden-5-ol, 1.47 g of phthalimide, and 2.62 g of triphenylphosphine in 15 ml of THF. The reaction mixture was allowed to stand overnight and then concentrated, the residue was stirred with ether, the precipitate was filtered off with suction, and the filtrate was concentrated. The residue was purified over silica gel using toluene. This gave 1.36 g of a yellow oil. concentrated the residue was stirred with ether the precipitate was filtered off with suction the filtrate was concentrated The residue was purified over silica gel

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 25 g of tricyclo[5.2.1.0 (2,6)]decan-8-one (Aldrich) were dissolved in 100 ml of methanol and, at room temperature and with slight cooling and stirring, admixed a little at a time with 6.3 g of solid sodium borohydride over a period of 2 h. The mixture was then stirred for another 2 h and allowed to stand overnight. With cooling, about 40 ml of 2 N HCl were then added dropwise, followed by 20 ml of water. The mixture was concentrated, the residue was admixed with ethyl acetate, and the ethyl acetate phase was washed once with water and once with sodium bicarbonate solution. The ethyl acetate phase was dried using magnesium sulfate and then filtered and concentrated. This gave 26 g of an oil which was purified by distillation under reduced pressure. This gave 20.7 g of an oily liquid (bp0.5 76° C.). with slight cooling of 2 h The mixture was then stirred for another 2 h With cooling The mixture was concentrated the ethyl acetate phase was washed once with water and once with sodium bicarbonate solution The ethyl acetate phase was dried filtered concentrated This gave 26 g of an oil which was purified by distillation under reduced pressure This gave 20.7 g of an oily liquid (bp0.5 76° C.)