反应详情

To a stirred solution of (3R) (1-(methoxycarbonyl)-4-adamantyl) 3-(isobutoxycarbonylamino)pyrrolidine-1-carboxylate (130 mg, 0.28 mmol) in THF (5 mL) and MeOH (10 mL) was added 5% aq NaOH (5 mL). The mixture was stirred at rt for 3 d. The mixture was concentrated under reduced pressure, diluted with water (15 mL) and washed with ether (80 mL). The aqueous layer was diluted with 10% aq citric acid (30 mL) and extracted with EtOAc (3×40 mL). The combined organic extracts were dried over MgSO4 and concentrated to leave (3R)-4-(3-(isobutoxycarbonylamino)pyrrolidine-1-carbonyloxy)adamantane-1-carboxylic acid (178 mg) as an oil.

1. concentrationThe mixture was concentrated under reduced pressure
2. additiondiluted with water (15 mL)
3. washwashed with ether (80 mL)
4. additionThe aqueous layer was diluted with 10% aq citric acid (30 mL)
5. extractionextracted with EtOAc (3×40 mL)
6. dry with materialThe combined organic extracts were dried over MgSO4
7. concentrationconcentrated