dicyclohexyl(ethyl)phosphane

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

Procedure: A mixture of chloro-1,5-cyclooctadiene iridium (I) dimer (34 mg, 51 μmol) and (S)-1-[(R)-2-di-(3,5-bis(trifluoromethyl)phenyl)phosphino)ferrocenyl]ethyldicyclohexylphosphine (44 mg, 51 μmol; Solvias AG, SL-J006-2) in a mixture of 1:2 toluene and methanol (100 mL; purged with nitrogen for 15 minutes) was sonicated under an atmosphere of nitrogen for 15 minutes. To the resultant mixture, iodine (0.39 g, 1.52 mmol) and 1-ethyl-5-methylpyrazin-2(1H)-one (7.0 g, 50.66 mmol) was added. The resultant mixture was heated in an oil bath at 50° C. under an atmosphere of hydrogen gas at 800 psi for 48 hours. The product mixture was filtered through a pad of Celite. The filtrate was concentrated under vacuum. The residue was treated with chloroform saturated with ammonia gas (100 mL). The resultant suspension was filtered through a pad of Celite, which was the rinsed with chloroform saturated with ammonia gas. The combined filtrate was concentrated under vacuum. The residue was concentrated as a solution in toluene for subsequent reaction. was sonicated under an atmosphere of nitrogen for 15 minutes The product mixture was filtered through a pad of Celite The filtrate was concentrated under vacuum The residue was treated with chloroform saturated with ammonia gas (100 mL) The resultant suspension was filtered through a pad of Celite, which rinsed with chloroform saturated with ammonia gas The combined filtrate was concentrated under vacuum The residue was concentrated as a solution in toluene for subsequent reaction

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

Procedure: In an autoclave (160 ml), a solution of 200 mg (0.41 mmol) of bis(1,5-cyclooctadiene)dirhodium(I) dichloride and 480 mg (0.81 mmol) of (R)-1-[(S)-2-diphenylphosphino)ferrocenyl]ethyl-dicyclohexylphosphine (IIIb, corresponding to an educt/catalyst molar ratio of 50) in 70 ml of degassed methanol was added to 5.00 g (40 mmol) of 3-quinuclidinone under argon. The mixture was hydrogenated for 22 hours at 75° C. and 50 bar of H2. After evaporation of the reaction solution, the pH was adjusted to 1 with 1N hydrochloric acid and the mixture was extracted three times with 50 ml of dichloromethane. The aqueous phase was adjusted to pH 14 with sodium hydroxide solution (30 percent) and evaporated to dryness. The residue was extracted four times with 100 ml of dichloromethane and the combined organic extracts were dried over MgSO4 and evaporated to give 3.40 g (67 percent) of (S)-3-quinuclidinol in the form of a white crystalline solid. Recrystallization from ethyl acetate gave 2.65 g (52 percent) of (S)-3-quinuclidinol with 7 percent ee. Other data concerning the product was: ##EQU7## After evaporation of the reaction solution the mixture was extracted three times with 50 ml of dichloromethane evaporated to dryness The residue was extracted four times with 100 ml of dichloromethane the combined organic extracts were dried over MgSO4 evaporated

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

Procedure: A mixture of chloro-1,5-cyclooctadiene iridium (I) dimer (34 mg, 51 μmol) and (S)-1-[(R)-2-di-(3,5-bis(trifluoromethyl)phenyl)phosphino)ferrocenyl]ethyldicyclohexylphosphine (44 mg, 51 μmol; Solvias AG, SL-J006-2) in a mixture of 1:2 toluene and methanol (100 mL; purged with nitrogen for 15 minutes) was sonicated under an atmosphere of nitrogen for 15 minutes. To the resultant mixture, iodine (0.39 g, 1.52 mmol) and 1-ethyl-5-methylpyrazin-2(1H)-one (7.0 g, 50.66 mmol) was added. The resultant mixture was heated in an oil bath at 50° C. under an atmosphere of hydrogen gas at 800 psi for 48 hours. The product mixture was filtered through a pad of Celite. The filtrate was concentrated under vacuum. The residue was treated with chloroform saturated with ammonia gas (100 mL). The resultant suspension was filtered through a pad of Celite, which was the rinsed with chloroform saturated with ammonia gas. The combined filtrate was concentrated under vacuum. The residue was concentrated as a solution in toluene for subsequent reaction. was sonicated under an atmosphere of nitrogen for 15 minutes The product mixture was filtered through a pad of Celite The filtrate was concentrated under vacuum The residue was treated with chloroform saturated with ammonia gas (100 mL) The resultant suspension was filtered through a pad of Celite, which rinsed with chloroform saturated with ammonia gas The combined filtrate was concentrated under vacuum The residue was concentrated as a solution in toluene for subsequent reaction