hydrogen; palladium on activated charcoal in methanol 1.5 h;

1: 79 percent / aq. NaOH / methanol; tetrahydrofuran / 3 h / 20 °C 2: 83 percent / hydrogen / palladium on carbon / methanol / 1.5 h View Scheme

1.1: N-methyl morpholine; isobutyl chloroformate / tetrahydrofuran / 0.17 h / -25 °C 1.2: 100 percent / N-methyl morpholine / tetrahydrofuran / 2 h / -25 °C 2.1: 79 percent / aq. NaOH / methanol; tetrahydrofuran / 3 h / 20 °C 3.1: 83 percent / hydrogen / palladium on carbon / methanol / 1.5 h View Scheme

1: 83 percent / TEA / H2O; acetonitrile / 20 h / Ambient temperature 2: 54 percent / H2 / Pd / acetic acid; methanol; H2O View Scheme

1: diethyl ether; aqueous NaOH 2: palladium; methanol; aqueous acetic acid / Hydrogenation View Scheme