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With sodium tetrahydroborate; In methanol; at 0 - 20℃;
To a solution of l -(2-bromophenyl) propane-2-one (30 g, 140 mmol)To a solution of l -(2-bromophenyl) propane-2-one (30 g, 140 mmol) in MeOH ( 100 ml) was added NaBH4 (6.09 g, 210 mmol) at 0C and stirred at room temperature for 2 h. The reaction mixture was quenched with water and concentrated under reduced pressure to afford crude compound. The title compound was purified by separation methods A, E and M (Yield 28.0 g). The enantiomer- 1 showed up at tt =7.86 min with Chiralcel OD-H (4.6X250mm) 5mu, hexane: 2-PrOH: TFA (90:5:0. 1), 1 ml/min. in MeOH ( 100 ml) was added NaBH4 (6.09 g, 210 mmol) at 0C and stirred at room temperature for 2 h. The reaction mixture was quenched with water and concentrated under reduced pressure to afford crude compound. The title compound was purified by separation methods A, E and M (Yield 28.0 g). The enantiomer- 1 showed up at tt =7.86 min with Chiralcel OD-H (4.6X250mm) 5mu, hexane: 2-PrOH: TFA (90:5:0. 1), 1 ml/min.
With hydroxylamine hydrochloride; sodium acetate; In methanol; at 20℃; for 18h;
Referential Example 15 (2-Methyl- 1 H-indol-4-yl)methanamine (105) step 1 : To a mixture of l-(2-bromophenyl)propan-2-one (1.5 g, 7.04 mmol) and NaOAc (693 mg, 8.45 mmol) in MeOH (50 mL) at RT was added hydroxylamine hydrochloride (539 mg, 7.8 mmol). After the reaction mixture was stirred at RT for 18 h, it was concentrated in vacuo. Water was added (100 mL), and the mixture was extracted with EtOAc (50 mL x 3), dried (MgSO i) and concentrated in vacuo to afford l-(2-bromophenyl)propan-2-one oxime as a yellow solid (1.51 g, 94 %). MS (ESI): m/z = 228.1 [M+l]+.
With hydroxylamine hydrochloride; sodium acetate; In methanol; water; at 20℃; for 15h;
A solution of 2-bromophenylacetone (5.00 g, 23.47 mmol), hydroxylamine hydrochloride (1.680 g, 24.17 mmol) and sodium acetate (1.981 g, 24.15 mmol) in methanol (160 mL) and water (8 mL) was stirred at ambient temperature for 15 hours. The solvent was removed in vacuo and the crude material was added to 500 mL of methyl tert-butyl ether and washed with 50 mL each of water, saturated aqueous sodium bicarbonate, and brine. The organics were dried over sodium sulfate, filtered, and concentrated to provide the title compound. MS (ESI+) m/z 228, 230 Br doublet (M+H)+.
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