Diisopropylamine → HCID 117723631, compound

Participants

Reaction Conditions

Reaction Steps

Diisopropylamine (0.66 ml, 4.69 mmol) was dissolved in THF (30 ml) and cooled to −78° C. nBuLi (2.13 ml, 2.20 M in cyclohexane, 4.69 mmol) was added drop-wise and the reaction mixture was stirred at −78° C. for 10 min, at 0° C. for 30 min, and re-cooled to −78° C. 3-Fluoro-pyridine (0.40 ml, 4.69 mmol) was added drop-wise over 5 min, and the reaction mixture was stirred for 45 min. A solution of N-Boc-4-piperidinecarboxaldehyde (1.00 g, 4.69 mmol) in THF (10 ml) was added and the reaction mixture was warmed to RT and stirred for 15 min. The reaction mixture was quenched with sat aq NH4OAc (10 mL), diluted with EtOAc (100 mL), washed with water (2×50 mL), dried (MgSO4) and concentrated in vacuo to give the title compound as an orange oil (1.42 g, 98%). LCMS (ES+): 255.0 [MH-t-Bu]+.

Provenance & Evidence