反应详情

At 0° C. lithium aluminium hydride (2.102 mL, 5.04 mmol) was added dropwise to a stirred solution of methyl 1-(1-methylethylsulfonamido)-2,3-dihydro-1H-indene-5-carboxylate (1 g, 3.36 mmol) in tetrahydrofuran (dry) (25 mL). Mixture warmed to rt and stirred for 4 hr. After this time the reaction mixture was again cooled to 0° C. and more lithium aluminium hydride (2.102 mL, 5.04 mmol) added and the whole stirred at room temperature for 30 min before being carefully quenched with H2O (10 mL) and 2N NaOH (10 mL). The resulting mixture was filtered and partitioned between EtOAc and brine. The organic layer was separated, dried on Na2SO4 and solvent evaporated in vacuo to give a dark yellow oil. Purification by flash chromatography (0-100% EtOAc in Hept.) afforded the title compound as a colourless oil (670 mg 2.5 mmol, 74%). MS (ESI): m/z [M−H]− 268.0.

1. temperatureAfter this time the reaction mixture was again cooled to 0° C.
2. stirringthe whole stirred at room temperature for 30 min
3. custombefore being carefully quenched with H2O (10 mL) and 2N NaOH (10 mL)
4. filtrationThe resulting mixture was filtered
5. custompartitioned between EtOAc and brine
6. customThe organic layer was separated
7. customdried on Na2SO4 and solvent
8. customevaporated in vacuo
9. customto give a dark yellow oil
10. customPurification by flash chromatography (0-100% EtOAc in Hept.)