perchloric acid in tetrachloromethane 10 h;

toluene-4-sulfonic acid

1: 1.) LDA / 1.) THF, hexane, -78 deg C, 20 min, 2.) THF, hexane, RT, 30 min 2: 59 percent / 60percent aq. HClO4 / CCl4 / 3 h / Ambient temperature View Scheme

hydrogen; Pd-BaSO4 in toluene 48 h;

deuterium; Pd-BaSO4 in toluene 48 h; Title compound not separated from byproducts;

N,N-bis[(2S)-2-N-tosyl-N-Li-amino-3-Me-butyl]-4-tosylamide; methyllithium; lithium bromide in tetrahydrofuran; diethyl ether T=-78°C; 1 h;

1: 3,4-dihydro-2-methyl-naphthalen-1-yl acetate With methyllithium; lithium bromide; 4-methyl-N-[(1S)-2-methyl-1-({((2S)-3-methyl-2-{[(4-methylphenyl)sulfonyl]amino}butyl)[(4-methylphenyl)sulfonyl]amino}methyl)propyl]benzenesulfonamide in tetrahydrofuran; diethyl ether T=-78°C; 1 h; 2: chloro-trimethyl-silane in tetrahydrofuran; diethyl ether T=-78°C; Title compound not separated from byproducts;