N-(2-hydroxypropyl)benzamide

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

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

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Prepare a solution of N-(2-hydroxypropyl)benzamide (8.22 g, 45.9 mmol) in methylene chloride (100 mL). Add N-methylmorpholine N-oxide (7.0 g, 60.0 mmol) followed by powdered 4 Å molecular sieves. Cool the mixture to 0° C. and add tetra-n-propylammonium perruthenate in one portion. Stir the mixture for 30 minutes and then warm to room temperature for 1 hour and filter through Celite®. Concentrate the filtrate and flash-chromatograph on silica gel eluting with 100% ethyl acetate to afford 6.1 g of N-(2-oxopropyl)benzamide as a white solid. MS: m/e=178 (MH+) warm to room temperature for 1 hour filter through Celite® Concentrate the filtrate and flash-chromatograph on silica gel eluting with 100% ethyl acetate

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Prepare a solution of N-(2-hydroxypropyl)benzamide (8.22 g, 45.9 mmol) in methylene chloride (100 mL). Add N-methylmorpholine N-oxide (7.0 g, 60.0 mmol) followed by powdered 4 Å molecular sieves. Cool the mixture to 0° C. and add tetra-n-propylammonium perruthenate in one portion. Stir the mixture for 30 minutes and then warm to room temperature for 1 hour and filter through Celite®. Concentrate the filtrate and flash-chromatograph on silica gel eluting with 100% ethyl acetate to afford 6.1 g of N-(2-oxopropyl)benzamide as a white solid. MS: m/e=178 (MH+) warm to room temperature for 1 hour filter through Celite® Concentrate the filtrate and flash-chromatograph on silica gel eluting with 100% ethyl acetate

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

Procedure: Prepare a solution of 1-amino-2-propanol (5.0 g, 66.6 mmol) in methylene chloride (250 mL) at 0° C. under nitrogen. Add Hünig's Base (11.6 mL, 66.6 mmol) followed by benzoyl chloride (7.7 mL, 66.6 mmol). Warm the reaction mixture to room temperature and stir overnight. Wash the solution sequentially with brine (100 mL) and 1M HCl (75 mL), dry (Na2SO4), filter, and concentrate to afford 10.0 g of N-(2-hydroxypropyl)benzamide. MS: m/e=180 (MH+) Wash the solution sequentially with brine (100 mL) and 1M HCl (75 mL) dry (Na2SO4) filter concentrate

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

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

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Prepare a solution of N-(2-hydroxypropyl)benzamide (8.22 g, 45.9 mmol) in methylene chloride (100 mL). Add N-methylmorpholine N-oxide (7.0 g, 60.0 mmol) followed by powdered 4 Å molecular sieves. Cool the mixture to 0° C. and add tetra-n-propylammonium perruthenate in one portion. Stir the mixture for 30 minutes and then warm to room temperature for 1 hour and filter through Celite®. Concentrate the filtrate and flash-chromatograph on silica gel eluting with 100% ethyl acetate to afford 6.1 g of N-(2-oxopropyl)benzamide as a white solid. MS: m/e=178 (MH+) warm to room temperature for 1 hour filter through Celite® Concentrate the filtrate and flash-chromatograph on silica gel eluting with 100% ethyl acetate

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

Procedure: Prepare a solution of 1-amino-2-propanol (5.0 g, 66.6 mmol) in methylene chloride (250 mL) at 0° C. under nitrogen. Add Hünig's Base (11.6 mL, 66.6 mmol) followed by benzoyl chloride (7.7 mL, 66.6 mmol). Warm the reaction mixture to room temperature and stir overnight. Wash the solution sequentially with brine (100 mL) and 1M HCl (75 mL), dry (Na2SO4), filter, and concentrate to afford 10.0 g of N-(2-hydroxypropyl)benzamide. MS: m/e=180 (MH+) Wash the solution sequentially with brine (100 mL) and 1M HCl (75 mL) dry (Na2SO4) filter concentrate

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

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