Thionyl Chloride → (1R)-1-[(2R)-2-(4,5-diphenyloxazol-2-yl)pyrrolidin-1-yl]-5-tert-butyldiphenylsilyloxy-1,2,3,4-tetrahydronaphthalene

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Reaction Steps

To a solution of (1R)-1-[[(1R)-4-hydroxy-1-(4,5-diphenyloxazol-2-yl) butyl]amino]-5-tert-butyldiphenylsilyloxy-1,2,3,4-tetrahydronaphthalene (2.6 g) in CH2Cl2 (50 ml) was added SOCl2 (3 ml). After being stirred for 12 hours, the solvent was removed. The residue was dissolved in N,N-dimethylformamide (DMF) (15 ml) and K2CO3 (2 g) was added to the solution. After being stirred for 4 hours at the room temperature, the solution was poured into the mixture of ethyl acetate and water. The organic layer was washed with water and brine, dried over MgSO4 and evaporated in vacuo. The residue was purified by chromatography on silica gel to afford (1R)-1-[(2R)-2-(4,5-diphenyloxazol-2-yl)pyrrolidin-1-yl]-5-tert-butyldiphenylsilyloxy-1,2,3,4-tetrahydronaphthalene (1.22 g). MS (m/z): 675 (M+) IR (Neat): 1560 cm-1NMR (CDCl3, δ): 1.75 (9H, s), 1.5-2.4 (8H, m), 2.7-3.2 (4H, m), 4.0-4.3 (2H, m), 6.15 (1H, d, J=8 Hz), 6.45 (1H, t, J=8 Hz), 6.92 (1H, d, J=8 Hz), 7.2-7.8 (20H, m)

Provenance & Evidence