Scheme 2. Scale-up reaction and product elaboration. Reagents and conditions: (i) NaBH3CN (5 equiv.), TFA, rt, 1 h. (ii) Pd/C (10 mol%) H2 (1 atm), MeOH, rt, 2 h. (iii) Pd/C (10 mol%) H2 (4 MPa), MeOH/EA, 60 °C, 36 h. (iv) Pd/C (10 mol%) H2 (4 MPa), MeOH, 60 °C, 36 h. (v) PtO2 (10 mol%), H2 (4 MPa), AcOH, 80 °C, 72 h. (vi) MeOTf (1.2 equiv.), Et2O, 0 °C to rt, 2 h; Pd(PPh3)2Cl2 (5 mol%), PhMgBr (2 equiv.), THF, rt, 2 h. (vii) Pd/C (10 mol%) H2 (4 MPa), MeOH/EA, 60 °C, 72 h. (viii) Pd/C (20 mol%) H2 (5 MPa), EtOH/EA, 80 °C, 96 h.
