CC(C)([O-])C.[K+].[C:7]([NH:10][C:11]([CH:14]1[CH2:19][CH2:18][CH:17]([C:20]([O:22][CH3:23])=[O:21])[CH2:16][CH2:15]1)([CH3:13])[CH3:12])(=[O:9])[CH3:8].Cl>CO>[C:7]([NH:10][C:11]([C@H:14]1[CH2:15][CH2:16][C@H:17]([C:20]([O:22][CH3:23])=[O:21])[CH2:18][CH2:19]1)([CH3:13])[CH3:12])(=[O:9])[CH3:8]Potassium tert-butoxide (30.0 g) was added to a solution (150 ml) of a cis- and trans- mixture of methyl 4-(1-acetamido-1-methylethyl)cyclohexanecarboxylate (30.8 g) in methanol and the mixture was refluxed under heating for 40 hours. After completion of the reaction, the residue obtained by concentration under reduced pressure was poured into ice water, neutralized with conc. hydrochloric acid and extracted with chloroform. The extract was washed with water, dried and concentrated under reduced pressure. The resultant crystals were recrystallized from methanol to give 24.5 g of methyl trans-4-(1-acetamido-1-methylethyl)cyclohexanecarboxylate.
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