N-methoxy-N-methylcycloheptanecarboxamide

Conditions: temp:-10.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of triethylsilylacetylene (4.78 ml, 14 mmol) in THF (10 ml) at −78° C. was added dropwise a solution of BuLi in hexane (8 ml, 13 mmol). After 30 minutes, the mixture was warmed to −10° C. and a solution of N-methoxy-N-methylcycloheptanecarboxamide (2 g, 10.8 mmol) in THF (10 ml) was added. The mixture was stirred for 30 minutes at −10° C., quenched by addition of aqueous saturated ammonium chloride, allowed to warm up to room temperature and diluted with ether. The layers were separated and the aqueous phase was extracted with ether. Combined organic layers were washed with brine, dried over Na2SO4 and concentrated. After purification by chromatography on silica gel (hexane/CH2Cl2 90/10), the 1-cycloheptyl-3-(trimethylsilyl)-2-propyn-1-one 28 was obtained as a colorless liquid (1.74 g, 72%). quenched by addition of aqueous saturated ammonium chloride to warm up to room temperature diluted with ether The layers were separated the aqueous phase was extracted with ether Combined organic layers were washed with brine dried over Na2SO4 concentrated After purification by chromatography on silica gel (hexane/CH2Cl2 90/10)

Conditions: temp:-78.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of N-methoxy-N-methylcycloheptanecarboxamide (1.11 g, 6 mmol) in ether (10 ml) was added dropwise at −78° C. to a solution of 3-lithiopyridine (prepared by addition of BuLi (3.75 ml, 6 mmol) to 3-bromopyridine (0.58 ml, 6 mmol) in ether (25 ml) at −78° C.). The mixture was stirred for 2 hours at −78° C., quenched by addition of aqueous saturated NH4Cl, allowed to warm to room temperature and diluted with ether. The layers were separated and the aqueous phase was extracted 3 times with ether. Combined organic layers were washed with brine, dried over Na2SO4 and concentrated. After purification by chromatography on silica gel (CH2Cl2), the cycloheptyl(3-pyridinyl)methanone 18 was obtained as a slightly yellow oil (490 mg, 40%). quenched by addition of aqueous saturated NH4Cl to warm to room temperature diluted with ether The layers were separated the aqueous phase was extracted 3 times with ether Combined organic layers were washed with brine dried over Na2SO4 concentrated After purification by chromatography on silica gel (CH2Cl2)

Conditions: temp:-10.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of triethylsilylacetylene (4.78 ml, 14 mmol) in THF (10 ml) at −78° C. was added dropwise a solution of BuLi in hexane (8 ml, 13 mmol). After 30 minutes, the mixture was warmed to −10° C. and a solution of N-methoxy-N-methylcycloheptanecarboxamide (2 g, 10.8 mmol) in THF (10 ml) was added. The mixture was stirred for 30 minutes at −10° C., quenched by addition of aqueous saturated ammonium chloride, allowed to warm up to room temperature and diluted with ether. The layers were separated and the aqueous phase was extracted with ether. Combined organic layers were washed with brine, dried over Na2SO4 and concentrated. After purification by chromatography on silica gel (hexane/CH2Cl2 90/10), the 1-cycloheptyl-3-(trimethylsilyl)-2-propyn-1-one 28 was obtained as a colorless liquid (1.74 g, 72%). quenched by addition of aqueous saturated ammonium chloride to warm up to room temperature diluted with ether The layers were separated the aqueous phase was extracted with ether Combined organic layers were washed with brine dried over Na2SO4 concentrated After purification by chromatography on silica gel (hexane/CH2Cl2 90/10)

Conditions: temp:-78.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of N-methoxy-N-methylcycloheptanecarboxamide (1.11 g, 6 mmol) in ether (10 ml) was added dropwise at −78° C. to a solution of 3-lithiopyridine (prepared by addition of BuLi (3.75 ml, 6 mmol) to 3-bromopyridine (0.58 ml, 6 mmol) in ether (25 ml) at −78° C.). The mixture was stirred for 2 hours at −78° C., quenched by addition of aqueous saturated NH4Cl, allowed to warm to room temperature and diluted with ether. The layers were separated and the aqueous phase was extracted 3 times with ether. Combined organic layers were washed with brine, dried over Na2SO4 and concentrated. After purification by chromatography on silica gel (CH2Cl2), the cycloheptyl(3-pyridinyl)methanone 18 was obtained as a slightly yellow oil (490 mg, 40%). quenched by addition of aqueous saturated NH4Cl to warm to room temperature diluted with ether The layers were separated the aqueous phase was extracted 3 times with ether Combined organic layers were washed with brine dried over Na2SO4 concentrated After purification by chromatography on silica gel (CH2Cl2)