Tetrabutylammonium Fluoride → Di-tert-butyl (1S,2S,5R,6S)-2-[(tert-butoxycarbonyl)amino]bicyclo[3.1.0]hex-3-ene-2,6-dicarboxylate

HRID 2172987ノート

反応式

HRID 2172987 の反応式
[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[C:19]([O:23][C:24]([NH:26][C@@:27]1([C:45]([O:47][C:48]([CH3:51])([CH3:50])[CH3:49])=[O:46])[CH2:32][C@H:31](OS(C)(=O)=O)[C@@H:30]2[C@H:28]1[C@H:29]2[C:38]([O:40][C:41]([CH3:44])([CH3:43])[CH3:42])=[O:39])=[O:25])([CH3:22])([CH3:21])[CH3:20]>O1CCCC1.O>[C:19]([O:23][C:24]([NH:26][C@@:27]1([C:45]([O:47][C:48]([CH3:51])([CH3:50])[CH3:49])=[O:46])[CH:32]=[CH:31][C@@H:30]2[C@H:28]1[C@H:29]2[C:38]([O:40][C:41]([CH3:43])([CH3:42])[CH3:44])=[O:39])=[O:25])([CH3:22])([CH3:20])[CH3:21]

参加物

5

反応物 2

HCID 2724141Tetrabutylammonium FluorideHCID 86695971HCID 86695971、化合物

生成物 1

HCID 71681345Di-tert-butyl (1S,2S,5R,6S)-2-[(tert-butoxycarbonyl)amino]bicyclo[3.1.0]hex-3-ene-2,6-dicarboxylate収率 48%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒2 回

実験手順

Add 1M tetrabutylammonium fluoride in tetrahydrofuran (3.84 mL, 3.84 mmol) to di-tert-butyl (1S,2S,4S,5R,6R)-2-[(tert-butoxycarbonyl)amino]-4-[(methylsulfonyl)oxy]bicyclo[3.1.0]hexane-2,6-dicarboxylate (600.00 mg, 1.22 mmol) in tetrahydrofuran (2.03 mL) and heat at reflux for 3 hours. The reaction is then cooled to room temperature, diluted with water, and extracted with ethyl acetate, washed with brine, dried over sodium sulfate, filtered, and concentrated under reduced pressure to give a residue. The residue is purified by flash chromatography eluting with 5-75% ethyl acetate in hexanes to give the title compound (0.23 g, 0.58 mmol, 48%).

後処理

  1. temperatureheat
  2. temperatureat reflux for 3 hours
  3. extractionextracted with ethyl acetate
  4. washwashed with brine
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customto give a residue
  9. customThe residue is purified by flash chromatography
  10. washeluting with 5-75% ethyl acetate in hexanes

出典と根拠

ORDレコード
ord-f31df39bb429447aaeab2ee101695153
出典データセット
uspto-grants-2015_06
特許番号
US09056844B2

反応ノート

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