1: 1.) LDA / 1.) THF, -70 deg C, 1 h, 2.) THF, -70 deg C, 1 h 2: 35percent H2O2, 1N aq. NaOH / 1 h / Ambient temperature 3: pyridine / 12 h / Ambient temperature 4: 85 percent / H2, aq. AcOH / 10percent Pd/C / dioxane / 15 h / 60 °C / 760 Torr View Scheme

1: 1.) lithium diisopropylamide (LDA) / 1.) THF, -70 deg C, 1 h, 2.) THF, -70 deg C, 1 h 2: 65 percent / 1 N aq. NaOH, 35percent H2O2 / 1 h / Ambient temperature View Scheme

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lithium diisopropyl amide 1.) THF, -70 deg C, 1 h, 2.) THF, -70 deg C, 1 h; Yield given. Multistep reaction;