lithium borohydride in tetrahydrofuran; toluene T=100°C; 2 h;

1.1: Br2 / methanol / 1 h / 20 °C 1.2: 26 percent / tetrahydrofuran / 0.5 h / 20 °C 2.1: 73 percent / LDA / cyclohexane; tetrahydrofuran / 20 h / Heating 3.1: 52 percent / Pd(OAc)2; Et3N; TBABr / dimethylformamide / 3 h / 80 °C 4.1: 71 percent / LiBH4 / tetrahydrofuran; toluene / 2 h / 100 °C View Scheme

1: 73 percent / LDA / cyclohexane; tetrahydrofuran / 20 h / Heating 2: 52 percent / Pd(OAc)2; Et3N; TBABr / dimethylformamide / 3 h / 80 °C 3: 71 percent / LiBH4 / tetrahydrofuran; toluene / 2 h / 100 °C View Scheme

1: 52 percent / Pd(OAc)2; Et3N; TBABr / dimethylformamide / 3 h / 80 °C 2: 71 percent / LiBH4 / tetrahydrofuran; toluene / 2 h / 100 °C View Scheme

1: With methanesulfonyl chloride; triethylamine in tetrahydrofuran T=-20°C; 0.5 h; 2: With dimethyl amine in tetrahydrofuran T=-20 - 30°C;