Dimethylamine → 1-(N,N-dimethylcarbamoyl)-3-nitroadamantane

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C(Cl)(=O)C.[CH3:5][NH:6][CH3:7].[C:8]([C:11]12[CH2:20][CH:15]3[CH2:16][CH:17]([CH2:19][C:13]([N+:21]([O-:23])=[O:22])([CH2:14]3)[CH2:12]1)[CH2:18]2)(O)=[O:9]>CN(C=O)C>[CH3:5][N:6]([CH3:7])[C:8]([C:11]12[CH2:20][CH:15]3[CH2:16][CH:17]([CH2:19][C:13]([N+:21]([O-:23])=[O:22])([CH2:14]3)[CH2:12]1)[CH2:18]2)=[O:9]

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실험 절차

In an atmosphere of nitrogen, 10 mmole of 1-carboxy-3-nitroadamantane obtained by the method of Example 43 was dissolved in 10 ml of DMF. To the mixture, 15 mmole of acetyl chloride was added dropwise over 30 minutes. The mixture was heated to begin to reflux around the conclusion of the addition. After refluxing for 2 hours, the mixture was cooled,and 25 mmole of dimethylamine was added dropwise over 30 minutes while retaining the temperature of the mixture at 10° C. or less followed by stirring for more 2 hours. As a result, the conversion of 1-carboxy-3-nitroadamantane was 99%, and 1-(N,N-dimethylcarbamoyl)-3-nitroadamantane (yield 95%) was formed.