Acetic Acid → tert-Butyl octahydro-1H-pyrrolo[3,2-b]pyridine-1-carboxylate

Participants

Reaction Steps

The product of Step 3 (2.66 g, 12.2 mmol) was added to a Parr shaker pressure vessel that was subsequently purged with nitrogen. Platinum (IV) oxide (0.277 g, 1.22 mmol) was added, followed by AcOH (27 mL). The vessel was placed on a Parr shaker apparatus and was sealed and evacuated and refilled with nitrogen 4 times (with shaking in between cycles). The vessel was then evacuated and refilled with hydrogen 4 times (with shaking in between cycles). The reaction was shaken under hydrogen pressure (approximately 60 psi; the vessel was recharged up to 60 psi as needed) for 48 hours. An additional amount of platinum (IV) oxide (0.277 g, 1.22 mmol) was added in order to drive the reaction to completion. After 24 hours, the reaction mixture was diluted with EtOAc (50 mL) and filtered through a Celite cartridge (Celite 545 Isolute®SPE column; Biotage, Inc.), rinsing the filter cake with additional EtOAc. The filtrate was concentrated in vacuo to a crude oil which was azeotroped with heptane several times until a constant weight was achieved, affording the desired product (HOAc salt). LRMS calc'd for C12H23N2O2 [M+H]+, 227; found 227.

Provenance & Evidence