反应详情

A flame dried 100-mL, round-bottom flask was charged with sodium hydride (1.45 g, 60.0 mmol) and trimethyloxosulfonium iodide (8.0 g, 36 mmol). The flask was evacuated and refilled with N2, and dry DMSO (50 mL) was added. The mixture was stirred at rt for 2 h to give a solution of the sulfur ylid. A second 100-mL, round-bottom flask was charged with tert-butyl (2S,4S)-4-((1-(3-methoxypropyl)-1H-indazol-6-yl)methyl)-5-methyl-1-oxohexan-2-ylcarbamate (830 mg, 1.92 mmol) and THF (10 mL). The flask was evacuated and refilled with N2, and the sulfur ylid solution (6.0 mL) was added through a cannula. The resulting mixture was stirred for 2-3 h at rt. The reaction mixture was quenched with brine and extracted with ethyl acetate (3×25 mL). The combined organic phases were dried over Na2SO4, filtered and concentrated in vacuo. The residue was purified by chromatography to afford tert-butyl (1S,3S)-3-((1-(3-methoxypropyl)-1H-indazol-6-yl)methyl)-4-methyl-1-((S)-oxiran-2-yl)pentylcarbamate (410 mg, 48%). 1H NMR (400 MHz, CDCl3): 0.81-0.92 (m, 5H), 1.26 (m, 2H), 1.47 (s, 6H), 1.65 (m, 6H), 2.17 (m, 2H), 2.68 (m, 1H), 2.95 (m, 1H), 3.30 (s, 3H), 4.11 (m, 1H), 4.47 (m, 2H), 6.99 (m, 1H), 7.21 (m, 1H), 7.60 (m, 1H), 7.95 (m, 1H); MS: 446 (M++1)

1. customThe flask was evacuated
2. additionrefilled with N2
3. additionthe sulfur ylid solution (6.0 mL) was added through a cannula
4. customThe reaction mixture was quenched with brine
5. extractionextracted with ethyl acetate (3×25 mL)
6. dry with materialThe combined organic phases were dried over Na2SO4
7. filtrationfiltered
8. concentrationconcentrated in vacuo
9. customThe residue was purified by chromatography