(S)-5-BROMO-2,3-DIHYDRO-1H-INDEN-1-AMINE

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], (S)-5-bromo-indan-1-ylamine has been coupled with 3-(2,2,2-trifluoro-acetylamino)-oxetane-3-carboxylic acid (prepared from 3-amino-oxetane-3-carboxylic acid and trifluoro-acetic acid ethyl ester in analogy to the procedure described for the preparation of intermediate A-1 [A]) to give 3-(2,2,2-trifluoro-acetylamino)-oxetane-3-carboxylic acid ((S)-5-bromo-indan-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 dark brown viscous oil. MS: 453.3 (M−H−). described for the preparation of intermediate A-1 [A])

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], (S)-5-bromo-indan-1-ylamine 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 ((S)-5-bromo-indan-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 solid. MS: 439.3 (MH+).

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

实验步骤: (S)-1-Azido-5-bromo-2,3-dihydro-1H-indene (8.09 g, 34.0 mmol) was dissolved in THF (155 ml), then water (17.2 ml) was added, followed by triphenylphosphine (9.8 g, 37.4 mmol). To this mixture, potassium hydroxide (1.0 N, 34.0 ml, 34.0 mmol) was added drop by drop below 25° C. and stirring continued over night at RT. The reaction mixture was then poured into H2O (150 ml) and extracted with EtOAc (2×100 ml). The organic layers were dried over MgSO4, filtered and concentrated in vacuo to give a crude product (17.34 g), which was purified by flash chromatography (silica gel, 100 g, 0% to 40% MeOH in CH2Cl2) to yield the title compound (5.81 g, 81%) as light yellow oil. MS: 211 (M+, 1Br). continued over night at RT extracted with EtOAc (2×100 ml) The organic layers were dried over MgSO4 filtered concentrated in vacuo to give a crude product (17.34 g), which was purified by flash chromatography (silica gel, 100 g, 0% to 40% MeOH in CH2Cl2)