1: H2 / Pd/C / tetrahydrofuran / 40 - 50 °C 2: LiAlH4 / tetrahydrofuran / 50 - 60 °C 3: HBr / 120 - 130 °C View Scheme

1: H2 / Pd/C 2: aq. KOH View Scheme

1: H2 / Pd/C / tetrahydrofuran / 40 - 50 °C 2: LiAlH4 / tetrahydrofuran / 50 - 60 °C 3: HBr / 120 - 130 °C 4: 1) lithium diisopropylamide / 1) hexane, THF, 50 deg C, 2.5 h, 2) THF, a) r.t., 2 h, b) 40 deg C, 1 h 5: PCl5 / 6 h / Ambient temperature 6: 75 percent / diethyl ether / 12 h / 0 °C View Scheme

1: piperidine / pyridine / 110 - 130 °C 2: SOCl2, DMF 3: Heating View Scheme

1: SOCl2, DMF 2: Heating View Scheme

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sodium t-butanolate

hydrogen; palladium on activated charcoal