N-methyloxolan-3-amine

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: Add benzotriazol-1-yloxytris(dimethylamino)phosphonium hexafluorophosphate (2.2 g, 5.0 mmol, 1.5 equiv) to a solution of 4-(3-phenyl-indole-1-sulfonyl)-benzoic acid (1.23 g, 3.26 mmol, 1 equiv), (tetrahydro-furan-3-yl)-methylamine (331 mg, 3.27 mmol, 1.0 equiv), and triethylamine (2.3 mL, 1.7 g, 17 mmol, 5.0 equiv) in anhydr CH2Cl2 (12 mL). After 1 h, rotary evaporate the reaction solution and transfer the resultant residue to a column of silica gel (235 mm×35 mm dia.) and elute (50-90% EtOAc/hex). This yields 486 mg (32.4%) of rac-4-(3-phenyl-indole-1-sulfonyl)-N-(tetrahydro-furan-3-ylmethyl)-benzamide as a yellow foam. MS (m/e): 460.96 (M+1); 459.04 (M−1). rotary evaporate the reaction solution elute (50-90% EtOAc/hex)

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: Following the procedures described in Steps D and E of Example 1, replacing in Step D ethyl 5-chloro-3-(chlorosulfonyl)-1-(phenylsulfonyl)-1H-indole-2-carboxylate with ethyl 5-bromo-3-(chlorosulfonyl)-1-(phenylsulfonyl)-1H-indole-2-carboxylate, and methylamine hydrochloride with (±)-N-methyl-N-tetrahydrofuran-3-ylamine, the title compound was obtained.

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: Add benzotriazol-1-yloxytris(dimethylamino)phosphonium hexafluorophosphate (2.2 g, 5.0 mmol, 1.5 equiv) to a solution of 4-(3-phenyl-indole-1-sulfonyl)-benzoic acid (1.23 g, 3.26 mmol, 1 equiv), (tetrahydro-furan-3-yl)-methylamine (331 mg, 3.27 mmol, 1.0 equiv), and triethylamine (2.3 mL, 1.7 g, 17 mmol, 5.0 equiv) in anhydr CH2Cl2 (12 mL). After 1 h, rotary evaporate the reaction solution and transfer the resultant residue to a column of silica gel (235 mm×35 mm dia.) and elute (50-90% EtOAc/hex). This yields 486 mg (32.4%) of rac-4-(3-phenyl-indole-1-sulfonyl)-N-(tetrahydro-furan-3-ylmethyl)-benzamide as a yellow foam. MS (m/e): 460.96 (M+1); 459.04 (M−1). rotary evaporate the reaction solution elute (50-90% EtOAc/hex)

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: Add benzotriazol-1-yloxytris(dimethylamino)phosphonium hexafluorophosphate (2.2 g, 5.0 mmol, 1.5 equiv) to a solution of 4-(3-phenyl-indole-1-sulfonyl)-benzoic acid (1.23 g, 3.26 mmol, 1 equiv), (tetrahydro-furan-3-yl)-methylamine (331 mg, 3.27 mmol, 1.0 equiv), and triethylamine (2.3 mL, 1.7 g, 17 mmol, 5.0 equiv) in anhydr CH2Cl2 (12 mL). After 1 h, rotary evaporate the reaction solution and transfer the resultant residue to a column of silica gel (235 mm×35 mm dia.) and elute (50-90% EtOAc/hex). This yields 486 mg (32.4%) of rac-4-(3-phenyl-indole-1-sulfonyl)-N-(tetrahydro-furan-3-ylmethyl)-benzamide as a yellow foam. MS (m/e): 460.96 (M+1); 459.04 (M−1). rotary evaporate the reaction solution elute (50-90% EtOAc/hex)