反应详情

A solution of (5R)-4-chloro-5-methyl-6,7-dihydro-5H-cyclopenta[d]pyrimidin-7-yl acetate (11.86 g, 52.33 mmol) in 2:1 THF:H2O (270 mL) was cooled to 0° C. and treated with lithium hydroxide hydrate (3.95 g, 94.2 mmol). The reaction was stirred at room temperature for 4 hours. The reaction was concentrated and diluted with water and acidified with 6N HCl to a pH of 6. The aqueous layer was extracted with EtOAc. The combined organics were washed with brine, dried MgSO4, filtered, and concentrated. The crude residue was chromatographed (Biotage 65) eluting with 30-50% EtOAc/hexane to give (5R)-4-chloro-5-methyl-6,7-dihydro-5H-cyclopenta[d]pyrimidin-7-ol (6.09 g, 63%).

1. concentrationThe reaction was concentrated
2. additiondiluted with water
3. extractionThe aqueous layer was extracted with EtOAc
4. washThe combined organics were washed with brine, dried MgSO4
5. filtrationfiltered
6. concentrationconcentrated
7. customThe crude residue was chromatographed (Biotage 65)
8. washeluting with 30-50% EtOAc/hexane