Chloride → (2S,5S)-tert-butyl 2-((tert-butyldimethylsilyloxy)methyl)-5-hydroxy-5,6-dihydropyridine-1(2H)-carboxylate

Participants

Reaction Steps

To a stirred solution of cerious chloride (4.36 g, 11.71 mmol) and (S)-tert-butyl 2-((tert-butyldimethylsilyloxy)methyl)-5-oxo-5,6-dihydropyridine-1(2H)-carboxylate (Intermediate 50, 4.00 g, 11.71 mmol) in 50 mL MeOH at 0° C., NaBH4 (0.443 g, 11.71 mmol) was added as a solid. The mixture was stirred at ambient temp for 15 minutes. The mixture was concentrated and diluted with 10% citric acid (aq), H2O and ethyl acetate. The organic layer was separated and washed with brine, dried over MgSO4, filtered and concentrated to give a residue which was purified by silica gel column (25 g, 20-40% Hex/EA) to give the desired product (2.6 g) as a colorless oil.

Provenance & Evidence