反应详情

Use of indan-2-yl-acetic acid (commercially available from Lancaster) (Intermediate SEVENTEEN-1) (1.58 g, 8.88 mmol) in THF (15 mL) was added dropwise to a solution of LiAlH4 (9 mL, 1M in Et2O) in THF (10 mL) at 0° C. The mixture was reacted for 2 h at rt and quenched with Rochelle's salt solution and extracted with Et2O (3×). The organic layer was dried over MgSO4, filtered and concentrated under vacuum. The alcohol (1.35 g, 94%) was used in the next step without further purification. A solution of 2-indan-2-yl-ethanol (1.35 g, 8.32 mmol) in 18 mL of CH2Cl2 and CH3CN (2 mL) was treated with 4 Å molecular sieves (4.2 g) N-methylmorpholine-N-oxide (1.5 g, 13.5 mmol) and TPAP: tetra-n-propylammonium perruthenate (VII) (commercially available from Aldrich) (0.3 g, 0.85 mmol). The mixture was stirred for 16 h at rt. The mixture was poured directly onto a column of silica gel and eluted with 10% EtOAc:hexane. To give indan-2-ylacetaldehyde (Intermediate SEVENTEEN-2), 1.25 g (˜90%). Indan-2-ylacetaldehyde (Intermediate SEVENTEEN-2) in Method A produced 4-indan-2-ylmethyl-1,3-dihydro-imidazole-2-thione (Compound 142).

1. customThe mixture was reacted for 2 h at rt
2. customquenched with Rochelle's salt solution
3. extractionextracted with Et2O (3×)
4. dry with materialThe organic layer was dried over MgSO4
5. filtrationfiltered
6. concentrationconcentrated under vacuum
7. customThe alcohol (1.35 g, 94%) was used in the next step without further purification
8. additionThe mixture was poured directly onto a column of silica gel
9. washeluted with 10% EtOAc