Lithium Hydroxide → (S)-6-(tert-Butoxycarbonyl)-4-oxo-4,6,7,8-tetrahydropyrrolo[1,2-a]pyrimidine-3-carboxylic acid

Participants

Reaction Steps

To a solution of 1f (14.15 g, 48.1 mmol) in 250 mL MeOH at 0° C. was slowly added aqueous LiOH (1M, 48 mL, 48 mmol) over 15 min. The reaction was allowed to warm to rt overnight with stirring. The organic solvent was removed in vacuo. The residual aqueous solution was partitioned with Et2O, then the organic phase was extracted with H2O (2×). The combined aqueous extract was acidified to pH 2 with 1N HCl. The aqueous phase was extracted with CHCl3 (3×). The combined organic extract was dried (MgSO4) and concentrated to afford 11.4 g (85%) of the acid, 1g, as a tan crystalline solid.

Provenance & Evidence