Sodium borohydride → (2S)-tert-butyl 2-((tert-butyldimethylsilyloxy)methyl)-5-hydroxy-4-(methoxymethyl)-5,6-dihydropyridine-1(2H)-carboxylate

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Reaction Conditions

Reaction Steps

(S)-tert-butyl 2-((tert-butyldimethylsilyloxy)methyl)-4-(methoxymethyl)-5-oxo-5,6-dihydropyridine-1(2H)-carboxylate) (Intermediate 69, crude, 16.73 g, 43.39 mmol) was dissolved in MeOH (100 mL), cooled to 0° C. and CeCl3 (10.69 g, 43.39 mmol) was added to give a solution. Then NaBH4 (1.642 g, 43.39 mmol) was added slowly as solid, and the mixture was stirred from 0° C. to rt for 30 min. The volatile solvent was removed. The white solid was redissolved in 200 mL EtOAc and washed with sat. NaHCO3, brine, dried over MgSO4, filtered and concentrated. The residue was purified by silica gel column (0-100% EA/Hex) to afford 13.78 g, 82% as an colorless oil.

Provenance & Evidence