N-methylamine hydrochloride; sodium acetate in methanol T=20°C; Condensation; 12 h;

sodium tetrahydroborate in tetrahydrofuran; methanol T=20°C; Reduction; 2 h;

1: 60 percent / NaBH4 / tetrahydrofuran; methanol / 2 h / 20 °C 2: 65 percent / CsF / acetonitrile / 16 h / 70 °C 3: 55 percent / zinc; acetic acid / 1 h / 20 °C View Scheme

1: 60 percent / NaBH4 / tetrahydrofuran; methanol / 2 h / 20 °C 2: 65 percent / CsF / acetonitrile / 16 h / 70 °C 3: 55 percent / zinc; acetic acid / 1 h / 20 °C 4: 63 percent / aq. ammonium acetate; TiCl3 / tetrahydrofuran / 16 h / 20 °C / pH 6 View Scheme

1: 60 percent / NaBH4 / tetrahydrofuran; methanol / 2 h / 20 °C 2: 65 percent / CsF / acetonitrile / 16 h / 70 °C View Scheme