sodium amide in tetrahydrofuran 24 h; Ambient temperature;

1: 60 percent / 25percent DIBAH / tetrahydrofuran; toluene / 1 h / -30 - -25 °C 2: 62 percent / p-TosOH, H2 / 10percent Pd-C / ethyl acetate 3: 57 percent / NaNH2 / tetrahydrofuran / 24 h / Ambient temperature View Scheme

1: 62 percent / p-TosOH, H2 / 10percent Pd-C / ethyl acetate 2: 57 percent / NaNH2 / tetrahydrofuran / 24 h / Ambient temperature View Scheme

hydrogen; palladium on activated charcoal in pentane