triethyl(hydroxy)silane

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:23.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a 1.0 L round bottom flask containing 2-(1-(tert-butyldimethylsilyloxy)cyclopropyl)acetaldehyde (5.00 g, 23.3 mmol) (crude 10.5 g with TESOH, 1H NMR showed about 50/50 sm to impurity) was added DCM (200 mL) and the mixture was allowed to stir at 23° C. for 5 min. At this time, (R)-2-methylpropane-2-sulfinamide (2.83 g, 23.3 mmol) and cupric sulfate anhydrous (2.58 ml, 58.3 mmol) were added and the reaction was allowed to stir for 40 h. The copper salts were removed by celite filtration. The filtrate was concentrated to give a yellow oil that was purified on a 330 g Isco column (5 to 20% EtOAc in hexanes) to afford the title compound as a colorless oil. to stir for 40 h The copper salts were removed by celite filtration The filtrate was concentrated to give a yellow oil that was purified on a 330 g Isco column (5 to 20% EtOAc in hexanes)

Conditions: temp:23.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a 1.0 L round bottom flask containing 2-(1-(tert-butyldimethylsilyloxy)cyclopropyl)acetaldehyde (5.00 g, 23.3 mmol) (crude 10.5 g with TESOH, 1H NMR showed about 50/50 sm to impurity) was added DCM (200 mL) and the mixture was allowed to stir at 23° C. for 5 min. At this time, (R)-2-methylpropane-2-sulfinamide (2.83 g, 23.3 mmol) and cupric sulfate anhydrous (2.58 ml, 58.3 mmol) were added and the reaction was allowed to stir for 40 h. The copper salts were removed by celite filtration. The filtrate was concentrated to give a yellow oil that was purified on a 330 g Isco column (5 to 20% EtOAc in hexanes) to afford the title compound as a colorless oil. to stir for 40 h The copper salts were removed by celite filtration The filtrate was concentrated to give a yellow oil that was purified on a 330 g Isco column (5 to 20% EtOAc in hexanes)

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

Procedure: Trifluoroacetic acid (0.5 ml) was added dropwise to a solution of N-(2-(3-methoxyphenyl)ethyl)-4-(2-(1-hydroxyethyl)-5-methoxybenzyl)piperidine (250 mg, 0.65 mmol) and triethylsilane (91 mg, 0.78 mmol) in dichloromethane (5 ml) under ice-cooling, and the reaction mixture was stirred as it was for 2 hours. Ethyl acetate and a saturated aqueous sodium hydrogencarbonate solution were added thereto to effect separation, and the organic layer was washed with a saturated aqueous sodium chloride solution, dried over anhydrous sodium sulfate, and then distilled under reduced pressure to remove the solvent. The residue was purified by a silica gel column chromatography (chloroform/methanol=50/1) to obtain a mixture of N-(2-(3-methoxyphenyl)ethyl)-4-(2-ethyl-5-methoxybenzyl)piperidine and triethylsilanol. This mixture was dissolved in dichloromethane (5 ml), followed by adding thereto a 1N hydrogen chloride-diethyl ether solution (1 ml, 1 mmol), and the solvent was distilled off under reduced pressure. The residue was suspended in diethyl ether and the precipitate was collected by filtration and washed with diethyl ether to obtain the title compound (209 mg, 79%) as white powder. cooling separation the organic layer was washed with a saturated aqueous sodium chloride solution dried over anhydrous sodium sulfate distilled under reduced pressure to remove the solvent The residue was purified by a silica gel column chromatography (chloroform/methanol=50/1) to obtain by adding the precipitate was collected by filtration washed with diethyl ether

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

Procedure: In a reactor were placed di-μ-chlorobis(1,5-cyclooctadiene)diiridium(I) [IrCl(cod)]2 (0.05 mmol), vinyl acetate (20 mmol), and toluene (3 ml). The mixture was raised in temperature to 40° C. in a nitrogen atmosphere, triethylsilane (Et3SiH) (5 mmol) was added thereto over one hour, and a reaction was carried out at 40° C. for one hour. After the reaction, the reaction mixture was analyzed by gas chromatography to find that vinyltriethylsilane was produced in a yield of 36% and tetraethylsilane and acetic ester of triethylsilanol were by-produced in yields of 7% and 12%, respectively. In a reactor were placed was added a reaction was carried out at 40° C. for one hour After the reaction

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

Procedure: In a reactor were placed triethylsilane (Et3SiH) (5 mmol), di-μ-chlorobis(1,5-cyclooctadiene)diiridium(I) [IrCl(cod)]2 (0.05 mmol), vinyl acetate (20 mmol), and toluene (3 ml), and a reaction was conducted at 40° C. in a nitrogen atmosphere for one hour. After the reaction, the reaction mixture was analyzed by gas chromatography to find that vinyltriethylsilane was produced in a yield of 20%, and tetraethylsilane and acetic ester of triethylsilanol were by-produced in yields of 9% and 14%, respectively. In a reactor were placed After the reaction

Conditions: temp:23.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a 1.0 L round bottom flask containing 2-(1-(tert-butyldimethylsilyloxy)cyclopropyl)acetaldehyde (5.00 g, 23.3 mmol) (crude 10.5 g with TESOH, 1H NMR showed about 50/50 sm to impurity) was added DCM (200 mL) and the mixture was allowed to stir at 23° C. for 5 min. At this time, (R)-2-methylpropane-2-sulfinamide (2.83 g, 23.3 mmol) and cupric sulfate anhydrous (2.58 ml, 58.3 mmol) were added and the reaction was allowed to stir for 40 h. The copper salts were removed by celite filtration. The filtrate was concentrated to give a yellow oil that was purified on a 330 g Isco column (5 to 20% EtOAc in hexanes)to afford the title compound as a colorless oil. to stir for 40 h The copper salts were removed by celite filtration The filtrate was concentrated to give a yellow oil that was purified on a 330 g Isco column (5 to 20% EtOAc in hexanes)

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

Procedure: In a reactor were placed di-μ-chlorobis(1,5-cyclooctadiene)diiridium(I) [IrCl(cod)]2 (0.05 mmol), vinyl acetate (20 mmol), and toluene (3 ml). The mixture was raised in temperature to 40° C. in a nitrogen atmosphere, triethylsilane (Et3SiH) (5 mmol) was added thereto over one hour, and a reaction was carried out at 40° C. for one hour. After the reaction, the reaction mixture was analyzed by gas chromatography to find that vinyltriethylsilane was produced in a yield of 36% and tetraethylsilane and acetic ester of triethylsilanol were by-produced in yields of 7% and 12%, respectively. In a reactor were placed was added a reaction was carried out at 40° C. for one hour After the reaction

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

Procedure: In a reactor were placed triethylsilane (Et3SiH) (5 mmol), di-μ-chlorobis(1,5-cyclooctadiene)diiridium(I) [IrCl(cod)]2 (0.05 mmol), vinyl acetate (20 mmol), and toluene (3 ml), and a reaction was conducted at 40° C. in a nitrogen atmosphere for one hour. After the reaction, the reaction mixture was analyzed by gas chromatography to find that vinyltriethylsilane was produced in a yield of 20%, and tetraethylsilane and acetic ester of triethylsilanol were by-produced in yields of 9% and 14%, respectively. In a reactor were placed After the reaction

Conditions: temp:23.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a 1.0 L round bottom flask containing 2-(1-(tert-butyldimethylsilyloxy)cyclopropyl)acetaldehyde (5.00 g, 23.3 mmol) (crude 10.5 g with TESOH, 1H NMR showed about 50/50 sm to impurity) was added DCM (200 mL) and the mixture was allowed to stir at 23° C. for 5 min. At this time, (R)-2-methylpropane-2-sulfinamide (2.83 g, 23.3 mmol) and cupric sulfate anhydrous (2.58 ml, 58.3 mmol) were added and the reaction was allowed to stir for 40 h. The copper salts were removed by celite filtration. The filtrate was concentrated to give a yellow oil that was purified on a 330 g Isco column (5 to 20% EtOAc in hexanes)to afford the title compound as a colorless oil. to stir for 40 h The copper salts were removed by celite filtration The filtrate was concentrated to give a yellow oil that was purified on a 330 g Isco column (5 to 20% EtOAc in hexanes)

Conditions: temp:23.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a 1.0 L round bottom flask containing 2-(1-(tert-butyldimethylsilyloxy)cyclopropyl)acetaldehyde (5.00 g, 23.3 mmol) (crude 10.5 g with TESOH, 1H NMR showed about 50/50 sm to impurity) was added DCM (200 mL) and the mixture was allowed to stir at 23° C. for 5 min. At this time, (R)-2-methylpropane-2-sulfinamide (2.83 g, 23.3 mmol) and cupric sulfate anhydrous (2.58 ml, 58.3 mmol) were added and the reaction was allowed to stir for 40 h. The copper salts were removed by celite filtration. The filtrate was concentrated to give a yellow oil that was purified on a 330 g Isco column (5 to 20% EtOAc in hexanes) to afford the title compound as a colorless oil. to stir for 40 h The copper salts were removed by celite filtration The filtrate was concentrated to give a yellow oil that was purified on a 330 g Isco column (5 to 20% EtOAc in hexanes)

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

Procedure: Trifluoroacetic acid (0.5 ml) was added dropwise to a solution of N-(2-(3-methoxyphenyl)ethyl)-4-(2-(1-hydroxyethyl)-5-methoxybenzyl)piperidine (250 mg, 0.65 mmol) and triethylsilane (91 mg, 0.78 mmol) in dichloromethane (5 ml) under ice-cooling, and the reaction mixture was stirred as it was for 2 hours. Ethyl acetate and a saturated aqueous sodium hydrogencarbonate solution were added thereto to effect separation, and the organic layer was washed with a saturated aqueous sodium chloride solution, dried over anhydrous sodium sulfate, and then distilled under reduced pressure to remove the solvent. The residue was purified by a silica gel column chromatography (chloroform/methanol=50/1) to obtain a mixture of N-(2-(3-methoxyphenyl)ethyl)-4-(2-ethyl-5-methoxybenzyl)piperidine and triethylsilanol. This mixture was dissolved in dichloromethane (5 ml), followed by adding thereto a 1N hydrogen chloride-diethyl ether solution (1 ml, 1 mmol), and the solvent was distilled off under reduced pressure. The residue was suspended in diethyl ether and the precipitate was collected by filtration and washed with diethyl ether to obtain the title compound (209 mg, 79%) as white powder. cooling separation the organic layer was washed with a saturated aqueous sodium chloride solution dried over anhydrous sodium sulfate distilled under reduced pressure to remove the solvent The residue was purified by a silica gel column chromatography (chloroform/methanol=50/1) to obtain by adding the precipitate was collected by filtration washed with diethyl ether