2-methoxynaphthalene-1-carbonyl chloride

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

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

Procedure: To a solution of 2-methoxy-naphthalene-1-carbonyl chloride (0.50 g, 2.27 mmol) in dry dichloromethane (5 mL) at 0° C. under a N2 atmosphere was added 2-(S)-methoxymethylpyrrolidine (0.32 g, 2.75 mmol) and triethylamine (0.47 mL, 3.39 mmol). The mixture was allowed to warm to rt and stirred overnight, after which time it was poured into N HCl (50 mL) and extracted with dichloromethane (3× 50 mL). The combined organic layers were dried over Na2SO4, and the crude product was purified by column chromatography on silica gel using a solvent gradient of 10-30% ethyl acetate in hexane. The title compound was obtained as a colorless solid (0.374 g, 55%). 1H NMR (300 MHz, CDCl3) δ 1.90 (m, 6H), 2.99 (m, 1H), 3.21 (m, 1H), 3.48 (m, 3H), 3.95 (m, 3H), 4.59 (m, 1H), 7.29 (m, 1H), 7.37 (m, 1H), 7.48 (m, 1H), 7.76 (m, 3H); MS (ESI) m/z=300 [M+H]. extracted with dichloromethane (3× 50 mL) The combined organic layers were dried over Na2SO4 the crude product was purified by column chromatography on silica gel using a solvent gradient of 10-30% ethyl acetate in hexane

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

Procedure: To a solution of 2-methoxy-naphthalene-1-carbonyl chloride (0.50 g, 2.27 mmol) in dry dichloromethane (5 mL) at 0° C. under a N2 atmosphere was added 2-(S)-methoxymethylpyrrolidine (0.32 g, 2.75 mmol) and triethylamine (0.47 mL, 3.39 mmol). The mixture was allowed to warm to rt and stirred overnight, after which time it was poured into N HCl (50 mL) and extracted with dichloromethane (3× 50 mL). The combined organic layers were dried over Na2SO4, and the crude product was purified by column chromatography on silica gel using a solvent gradient of 10-30% ethyl acetate in hexane. The title compound was obtained as a colorless solid (0.374 g, 55%). 1H NMR (300 MHz, CDCl3) δ 1.90 (m, 6H), 2.99 (m, 1H), 3.21 (m, 1H), 3.48 (m, 3H), 3.95 (m, 3H), 4.59 (m, 1H), 7.29 (m, 1H), 7.37 (m, 1H), 7.48 (m, 1H), 7.76 (m, 3H); MS (ESI) m/z=300 [M+H]. extracted with dichloromethane (3× 50 mL) The combined organic layers were dried over Na2SO4 the crude product was purified by column chromatography on silica gel using a solvent gradient of 10-30% ethyl acetate in hexane

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

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

Procedure: To a solution of 2-methoxy-naphthalene-1-carbonyl chloride (0.50 g, 2.27 mmol) in dry dichloromethane (5 mL) at 0° C. under a N2 atmosphere was added 2-(S)-methoxymethylpyrrolidine (0.32 g, 2.75 mmol) and triethylamine (0.47 mL, 3.39 mmol). The mixture was allowed to warm to rt and stirred overnight, after which time it was poured into N HCl (50 mL) and extracted with dichloromethane (3×50 mL). The combined organic layers were dried over Na2SO4, and the crude product was purified by column chromatography on silica gel using a solvent gradient of 10-30% ethyl acetate in hexane. The title compound was obtained as a colorless solid (0.374 g, 55%). 1H NMR (300 MHz, CDCl3) δ 1.90 (m, 6 H), 2.99 (m, 1 H), 3.21 (m, 1 H), 3.48 (m, 3 H), 3.95 (m, 3 H), 4.59 (m, 1 H), 7.29 (m, 1 H), 7.37 (m, 1 H), 7.48 (m, 1 H), 7.76 (m, 3 H); MS (ESI) m/z=300 [M+H]. extracted with dichloromethane (3×50 mL) The combined organic layers were dried over Na2SO4 the crude product was purified by column chromatography on silica gel using a solvent gradient of 10-30% ethyl acetate in hexane

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

Procedure: To a solution of 2-methoxy-naphthalene-1-carbonyl chloride (0.50 g, 2.27 mmol) in dry dichloromethane (5 mL) at 0° C. under a N2 atmosphere was added 2-(S)-methoxymethylpyrrolidine (0.32 g, 2.75 mmol) and triethylamine (0.47 mL, 3.39 mmol). The mixture was allowed to warm to rt and stirred overnight, after which time it was poured into N HCl (50 mL) and extracted with dichloromethane (3×50 mL). The combined organic layers were dried over Na2SO4, and the crude product was purified by column chromatography on silica gel using a solvent gradient of 10-30% ethyl acetate in hexane. The title compound was obtained as a colorless solid (0.374 g, 55%). 1H NMR (300 MHz, CDCl3) δ 1.90 (m, 6 H), 2.99 (m, 1 H), 3.21 (m, 1 H), 3.48 (m, 3 H), 3.95 (m, 3 H), 4.59 (m, 1 H), 7.29 (m, 1 H), 7.37 (m, 1 H), 7.48 (m, 1 H), 7.76 (m, 3 H); MS (ESI) m/z=300 [M+H]. extracted with dichloromethane (3×50 mL) The combined organic layers were dried over Na2SO4 the crude product was purified by column chromatography on silica gel using a solvent gradient of 10-30% ethyl acetate in hexane

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

Procedure: To a solution of 2-methoxy-naphthalene-1-carbonyl chloride (0.50 g, 2.27 mmol) in dry dichloromethane (5 mL) at 0° C. under a N2 atmosphere was added 2-(S)-methoxymethylpyrrolidine (0.32 g, 2.75 mmol) and triethylamine (0.47 mL, 3.39 mmol). The mixture was allowed to warm to rt and stirred overnight, after which time it was poured into N HCl (50 mL) and extracted with dichloromethane (3× 50 mL). The combined organic layers were dried over Na2SO4, and the crude product was purified by column chromatography on silica gel using a solvent gradient of 10-30% ethyl acetate in hexane. The title compound was obtained as a colorless solid (0.374 g, 55%). 1H NMR (300 MHz, CDCl3) δ 1.90 (m, 6H), 2.99 (m, 1H), 3.21 (m, 1H), 3.48 (m, 3H), 3.95 (m, 3H), 4.59 (m, 1H), 7.29 (m, 1H), 7.37 (m, 1H), 7.48 (m, 1H), 7.76 (m, 3H); MS (ESI) m/z=300 [M+H]. extracted with dichloromethane (3× 50 mL) The combined organic layers were dried over Na2SO4 the crude product was purified by column chromatography on silica gel using a solvent gradient of 10-30% ethyl acetate in hexane