Water → tert-butyl N-[3-(N-methoxy-N-methylcarbamoyl)cyclohexyl]-N-methylcarbamate

HRID 1767325ノート

反応式

HRID 1767325 の反応式
[H-].[Na+].[CH3:3][O:4][N:5]([CH3:22])[C:6]([CH:8]1[CH2:13][CH2:12][CH2:11][CH:10]([NH:14][C:15](=[O:21])[O:16][C:17]([CH3:20])([CH3:19])[CH3:18])[CH2:9]1)=[O:7].[CH3:23]I.O>C1COCC1>[CH3:3][O:4][N:5]([CH3:22])[C:6]([CH:8]1[CH2:13][CH2:12][CH2:11][CH:10]([N:14]([CH3:23])[C:15](=[O:21])[O:16][C:17]([CH3:19])([CH3:18])[CH3:20])[CH2:9]1)=[O:7]

参加物

6

反応物 4

HCID 962WaterHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 22258796Tert-butyl 3-([methoxy(methyl)amino]carbonyl}cyclohexylcarbamate

生成物 1

HCID 22258869tert-butyl N-[3-(N-methoxy-N-methylcarbamoyl)cyclohexyl]-N-methylcarbamate収率 93%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
60 °C

実験手順

To a suspension of NaH (60%, 340 mg, 8.38 mmol) in THF (10 mL) was added dropwise a solution of tert-butyl 3-{[methoxy(methyl)amino]carbonyl}cyclo-hexylcarbamate (2.00 g, 6.98 mmol) in THF (10 mL) followed by methyl iodide (1.09 g, 7.68 mmol). The mixture was stirred at 60° C. for 0.5 hr. After cooled to room temperature, the mixture was poured into water and extracted with ethyl acetate. The organic phase was washed with brine, dried over Na2SO4, filtered and evaporated. The residue was purified by column chromatography on silica gel (hexane/ethyl acetate=1/1) to give tert-butyl N-[3-(N-methoxy-N-methyl-carbamoyl)cyclohexyl]-N-methylcarbamate as a colorless oil (1.94 g, yield; 93%).

後処理

  1. temperatureAfter cooled to room temperature
  2. extractionextracted with ethyl acetate
  3. washThe organic phase was washed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue was purified by column chromatography on silica gel (hexane/ethyl acetate=1/1)

出典と根拠

ORDレコード
ord-6784fd6cf42e429a96eaf44c3de1800e
出典データセット
uspto-grants-2007_06
特許番号
US07232909B2

反応ノート

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