tert-butyl 4-(5-methoxy-1-(triisopropylsilyl)-1H-pyrrolo[3,2-b]pyridin-6-yl)-5,6-dihydropyridine-1(2H)-carboxylate → tert-butyl 4-(5-methoxy-1-(triisopropylsilyl)-1H-pyrrolo[3,2-b]pyridin-6-yl)piperidine-1-carboxylate

Participants

Reaction Steps

To colorless solution of tert-butyl 4-(5-methoxy-1-(triisopropylsilyl)-1H-pyrrolo[3,2-b]pyridin-6-yl)-5,6-dihydropyridine-1(2H)-carboxylate (998 mg, 2.055 mmol) in MeOH (30 mL) was added platinum(IV) oxide (98 mg, 0.432 mmol) at rt. The mixture was shaked on Par Shaker for 3 hr under H2 (55 psi). The mixture was filtered with MeOH (20 mL), concentrated on rotary vacuo to afford the expected product, tert-butyl 4-(5-methoxy-1-(triisopropylsilyl)-1H-pyrrolo[3,2-b]pyridin-6-yl)piperidine-1-carboxylate (995 mg, 100%) as a light grey solid. Mass spec 488.27 Calc for C27H45N3O3Si 487.32, which was pure enough to be used in next reaction.

Provenance & Evidence