N,N-di(propan-2-yl)butan-1-amine

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

Procedure: To a solution of 3-hydroxy-1-(pyrrolidin-1-yl)methyl-3-hydroxybenzene (0.95 g) in dry dimethylformamide (5 ml) was added by syringe, with stirring, diisopropylbutylamine (1.1 ml) followed by triisopropylsilyl chloride (0.97 ml). The reaction mixture was stirred at ambient temperature for 1 hr, ice (10 g) was added and after stirring for 10 mins, the mixture was poured into ice/water and extracted with ethyl acetate. The extract was washed with water, saturated sodium chloride solution, dried over anhydrous sodium sulfate, filtered, and the filtrate was concentrated. The residue was flash column chromatographed (silica gel) eluting with dichloromethane, 1%, 2% and 5% methanol/dichloromethane. The appropriate fractions were collected and concentrated to give 0.65 g of product. Additional fractions were collected, concentrated and chromatographed over silica gel. Concentration of the appropriate fractions gave 0.15 g of product. Total yield 0.80 g (50%). The reaction mixture was stirred at ambient temperature for 1 hr after stirring for 10 mins extracted with ethyl acetate The extract was washed with water, saturated sodium chloride solution dried over anhydrous sodium sulfate filtered the filtrate was concentrated chromatographed (silica gel) eluting with dichloromethane, 1%, 2% and 5% methanol/dichloromethane The appropriate fractions were collected concentrated

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

Procedure: To a solution of 3-hydroxy-1-(pyrrolidin-1-yl)methyl-3-hydroxybenzene (0.95 g) in dry dimethylformamide (5 ml) was added by syringe, with stirring, diisopropylbutylamine (1.1 ml) followed by triisopropylsilyl chloride (0.97 ml). The reaction mixture was stirred at ambient temperature for 1 hr, ice (10 g) was added and after stirring for 10 mins, the mixture was poured into ice/water and extracted with ethyl acetate. The extract was washed with water, saturated sodium chloride solution, dried over anhydrous sodium sulfate, filtered, and the filtrate was concentrated. The residue was flash column chromatographed (silica gel) eluting with dichloromethane, 1%, 2% and 5% methanol/dichloromethane. The appropriate fractions were collected and concentrated to give 0.65 g of product. Additional fractions were collected, concentrated and chromatographed over silica gel. Concentration of the appropriate fractions gave 0.15 g of product. Total yield 0.80 g (50%). The reaction mixture was stirred at ambient temperature for 1 hr after stirring for 10 mins extracted with ethyl acetate The extract was washed with water, saturated sodium chloride solution dried over anhydrous sodium sulfate filtered the filtrate was concentrated chromatographed (silica gel) eluting with dichloromethane, 1%, 2% and 5% methanol/dichloromethane The appropriate fractions were collected concentrated

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

Procedure: To a solution of 3-hydroxy-1-(pyrrolidin-1-yl)methyl-3-hydroxybenzene (0.95 g) in dry dimethylformamide (5 ml) was added by syringe, with stirring, diisopropylbutylamine (1.1 ml) followed by triisopropylsilyl chloride (0.97 ml). The reaction mixture was stirred at ambient temperature for 1 hr, ice (10 g) was added and after stirring for 10 mins, the mixture was poured into ice/water and extracted with ethyl acetate. The extract was washed with water, saturated sodium chloride solution, dried over anhydrous sodium sulfate, filtered, and the filtrate was concentrated. The residue was flash column chromatographed (silica gel) eluting with dichloromethane, 1%, 2% and 5% methanol/dichloromethane. The appropriate fractions were collected and concentrated to give 0.65 g of product. Additional fractions were collected, concentrated and chromatographed over silica gel. Concentration of the appropriate fractions gave 0.15 g of product. Total yield 0.80 g (50%). The reaction mixture was stirred at ambient temperature for 1 hr after stirring for 10 mins extracted with ethyl acetate The extract was washed with water, saturated sodium chloride solution dried over anhydrous sodium sulfate filtered the filtrate was concentrated chromatographed (silica gel) eluting with dichloromethane, 1%, 2% and 5% methanol/dichloromethane The appropriate fractions were collected concentrated