formic acid; hydrogen; platinum on activated charcoal in methanol T=20°C; P=2585.74 Torr; 4 h;

1: 1,2,3,4-tetrahydro-1,4-methano-naphthalene-cis-2,3-diol With sodium periodate; N-benzyl-N,N,N-triethylammonium chloride in dichloromethane; water T=10 - 25°C; 2: benzylamine With sodium tetrahydroborate; acetic acid in dichloromethane T=20 - 25°C; 1 h; 3: With sodium carbonate in dichloromethane; water T=20 - 25°C; pH=8 - 9; 1 h; Product distribution / selectivity;

1: 89 percent / aq. OsO4; N-methylmorpholine-N-oxide / acetone; 2-methyl-propan-2-ol / 60 h 2: aq. NaIO4; Et3BnNCl / 1,2-dichloro-ethane / 1 h 3: 48.5 g / NaBH(OAc)3 / 1,2-dichloro-ethane / 20 °C View Scheme

1: 89 percent / n-BuLi / toluene; hexane / 20 °C 2: 89 percent / aq. OsO4; N-methylmorpholine-N-oxide / acetone; 2-methyl-propan-2-ol / 60 h 3: aq. NaIO4; Et3BnNCl / 1,2-dichloro-ethane / 1 h 4: 48.5 g / NaBH(OAc)3 / 1,2-dichloro-ethane / 20 °C View Scheme

in diethyl ether; water

1: aq. NaIO4; Et3BnNCl / 1,2-dichloro-ethane / 1 h 2: 48.5 g / NaBH(OAc)3 / 1,2-dichloro-ethane / 20 °C View Scheme

1: 89 percent / n-BuLi / toluene; hexane / 20 °C 2: 89 percent / aq. OsO4; N-methylmorpholine-N-oxide / acetone; 2-methyl-propan-2-ol / 60 h 3: aq. NaIO4; Et3BnNCl / 1,2-dichloro-ethane / 1 h 4: 48.5 g / NaBH(OAc)3 / 1,2-dichloro-ethane / 20 °C View Scheme

hydrogenchloride; hydrogen; palladium(II) oxide hydrate in methanol T=20 - 40°C; P=3677.86 - 4413.43 Torr;