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Reagents and conditions: (i) a, TBTU, DCM, TEA, 0 °C, 1 h; b, PQ, DCM, TEA, rt. (ii) CH3NHOMe, TBTU, DCM, TEA, rt, 7 h. (iii) LiAlH4, THF, 0 °C, 1 h. (iv) a, PQ, DCM, rt, 30 min; b, NaBH(AcO)3, AcOH, rt, 16 h. (v) a, CH3OCOCl, TEA, DCM, 0 °C 1 h; b PQ, 0 °C 30 min, rt, 1.5 h.
