反应详情

LiOH—H2O (0.499 g, 11.9 mmol) was added to a 0° C. solution of tert-butyl 4-((5R,7R)-5-methyl-7-(4-nitrobenzoyloxy)-6,7-dihydro-5H-cyclopenta[d]pyrimidin-4-yl)piperazine-1-carboxylate (2.30 g, 4.76 mmol) in 2:1 THF:H2O (40 mL). The reaction mixture was warmed to room temperature and stirred for 1 hour. The THF was removed by rotary evaporation, and saturated NaHCO3 was added. The mixture was extracted with ethyl acetate. The combined extracts were washed with saturated NaHCO3 (1×), dried (Na2SO4), filtered, and concentrated to give tert-butyl 4-((5R,7R)-7-hydroxy-5-methyl-6,7-dihydro-5H-cyclopenta[d]pyrimidin-4-yl)piperazine-1-carboxylate (1.59 g, 100.0% yield) as a yellow foam. LC/MS (APCI+) m/z 335 [M+H]+. The tert-butyl 4-((5R,7S)-7-hydroxy-5-methyl-6,7-dihydro-5H-cyclopenta[d]pyrimidin-4-yl)piperazine-1-carboxylate was prepared using a analogous method.

1. customThe THF was removed by rotary evaporation, and saturated NaHCO3
2. additionwas added
3. extractionThe mixture was extracted with ethyl acetate
4. washThe combined extracts were washed with saturated NaHCO3 (1×)
5. dry with materialdried (Na2SO4)
6. filtrationfiltered
7. concentrationconcentrated