CO[CH:3]1[CH2:7][CH2:6][CH:5](OC)[O:4]1.[CH:10]([NH:13][CH:14]([CH3:16])[CH3:15])([CH3:12])[CH3:11].Cl.C(C(O)=O)C(CC(O)=O)=O.C([O-])(=O)C.[Na+]>Cl.O>[CH:10]([N:13]1[CH:6]2[CH2:5][CH2:16][CH:14]1[CH2:15][C:3](=[O:4])[CH2:7]2)([CH3:12])[CH3:11]2M Hydrochloric acid (8 drops) was added to a stirred solution of 2,5-dimethoxytetrahydrofuran (16.5 g) in water (70 ml). After 15 minutes a mixture of diisopropylamine (7.38 g) and 2M hydrochloric acid (40 ml) was added to the reaction followed by acetonedicarboxylic acid (18.25 g) and sodium acetate (10.0 g) in water (100 ml). After 3 days 1,3-acetonedicarboxylic acid (6.0 g) and sodium acetate (3.0 g) were added. After a further 6 days the mixture was basified to pH8 and extracted with ethyl acetate. The extracts were dried (MgSO4) and evaporated under reduced pressure. The aqueous fraction was then extracted with chloroform and the extracts dried (MgSO4) and evaporated under reduced pressure. Distillation of the combined extracts (95-115° C.; 18 mmHg) gave 8-isopropyl-8-azabicyclo[3.2.1]octan-3-one (3.37 g).
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