反应详情

Ethyl-1-((1-(1-methylethylsulfonamido)-2,3-dihydro-1H-inden-5-yl)methyl)-3-(trifluoro methyl)-1H-pyrazole-4-carboxylate (0.196 mmol, 90 mg) was dissolved in THF (5 mL) and cooled in an ice bath under nitrogen. Di-isobutyl aluminium hydride (0.588 mmol, 0.588 mL) was added dropwise and the reaction stirred for 1.5 h. The reaction mixture was warmed to room temperature and stirred for a further 30 min before an additional 0.2 ml of di-isobutyl aluminium hydride was added and stirring continued for 30 min before quenching with MeOH followed by water. The mixture was concentrated before partitioning between EtOAc/water. The aq. layer was acidified with 5N HCl until all solids were in solution. The organic phase was collected, dried and concentrated and the residue purified by HPLC to give a colourless oil which crystallised on standing (63 mg, 0.151 mmol, 77%). 1H NMR (400 MHz, CDCl3) δ 1.43 (d, 6H) 1.95 (m, 1H) 2.65 (m, 1H) 2.80 (m, 1H) 3.00 (m, 1H), 3.24 (m, 1H) 4.20 (d, 1H) 4.65 (s, 2H) 4.95 (q, 1H) 5.28 (s, 2H) 7.13 (m, 2H) 7.44 (m, 2H).

1. temperaturecooled in an ice bath under nitrogen
2. additionwas added
3. stirringstirring
4. waitcontinued for 30 min
5. custombefore quenching with MeOH
6. concentrationThe mixture was concentrated
7. custombefore partitioning between EtOAc/water
8. customThe organic phase was collected
9. customdried
10. concentrationconcentrated
11. customthe residue purified by HPLC
12. customto give a colourless oil which
13. customcrystallised