1: 100 percent / SOCl2, Et3N / CH2Cl2 / 3 h 2: NaN3 / dimethylformamide / 6 h / 50 °C 3: 96 percent / Et3N / CH2Cl2 / 0 °C 4: H2 / Pd/C 5: 1.) diethyl azodicarboxylate, PPh3, 2.) 1N aq. NaOH / 2.) MeOH, 2 h View Scheme

With  osmium(VIII) oxide; methanesulfonamide; (9-O-indolinylcarbamoyl)dihydroquinidine (DHQD-IND); potassium carbonate; potassium hexacyanoferrate(III) in  water; toluene; tert-butyl alcohol T=0°C;  Yield given. Yields of byproduct given. Title compound not separated from byproducts;   

With  osmium(VIII) oxide; methanesulfonamide; (9-O-indolinylcarbamoyl)dihydroquinidine (DHQD-IND); potassium carbonate; potassium hexacyanoferrate(III) in  water; toluene; tert-butyl alcohol T=0°C;  Yield given. Yields of byproduct given. Title compound not separated from byproducts;