6-溴-1,2,3,4-四氢萘-1-胺

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

实验步骤: In analogy to the procedure described for the preparation of intermediate A-1 [B] and A-1 [C], (rac)-6-bromo-1,2,3,4-tetrahydronaphthalen-1-amine has been coupled with 1-(2,2,2-trifluoroacetamido)cyclopropanecarboxylic acid (intermediate A-1 [A]) to give 1-(2,2,2-trifluoro-acetylamino)-cyclopropanecarboxylic acid ((rac)-6-bromo-1,2,3,4-tetrahydro-naphthalen-1-yl)-amide, which was subsequently reacted with 4,4,4′,4′,5,5,5′,5′-octamethyl-2,2′-bi(1,3,2-dioxaborolane) to yield the title compound as light brown oil. MS: 453.2 (MH+).

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

实验步骤: 6-Bromo-3,4-dihydro-2H-naphthalen-1-one (9.5 g, 42.2 mmol) was suspended in 2-propanol (250 ml); then, NaBH3 CN (13.3 g, 211 mmol) was added, followed by ammonium acetate (65.1 g, 844 mmol). The reaction mixture was then stirred at RT for 4 hours. It was subsequently heated up to reflux and stirring was continued for 22 hours. The reaction mixture was then cooled down to RT and poured into cold H2O (500 ml); the pH was adjusted to >10 with sodium hydroxide solution and the mixture was extracted with CH2Cl2 (2×25 ml). The organic layers were dried over MgSO4, filtered and concentrated in vacuo to give a crude product (9.842 g) which was purified by flash chromatography (silica gel, 100 g, 2% to 10% MeOH in CH2Cl2) to yield the title compound (8.08 g, 85%) as light red oil. MS: 226.0 (MH+, 1Br). It was subsequently heated up to reflux stirring was continued for 22 hours The reaction mixture was then cooled down to RT the mixture was extracted with CH2Cl2 (2×25 ml) The organic layers were dried over MgSO4 filtered concentrated in vacuo to give a crude product (9.842 g) which was purified by flash chromatography (silica gel, 100 g, 2% to 10% MeOH in CH2Cl2)