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Triethylammonium formate → (S)-tert-butyl 2,2-dimethyl-4-(((S)-tetrahydrofuran-3-yl)methyl)oxazolidine-3-carboxylate

HRID 451826
ノート
印刷プレビュー

反応式

HRID 451826 の反応式
[Si](O[CH2:9][C@H:10]([CH2:26][CH2:27][O:28]S(C)(=O)=O)[CH2:11][C@H:12]1[CH2:16][O:15][C:14]([CH3:18])([CH3:17])[N:13]1[C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])(C(C)(C)C)(C)C.CCN(CC)CC.C(O)=O>C1COCC1.CC(=O)OCC>[CH3:18][C:14]1([CH3:17])[N:13]([C:19]([O:21][C:22]([CH3:23])([CH3:24])[CH3:25])=[O:20])[C@@H:12]([CH2:11][C@H:10]2[CH2:26][CH2:27][O:28][CH2:9]2)[CH2:16][O:15]1
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 2

HCID 11084032Triethylammonium formateHCID 86639451(S)-tert-butyl 4-((S)-2-((tert-butyldimethylsilyloxy)methyl)-4-(methylsulfonyloxy)butyl)-2,2-dimethyloxazolidine-3-carboxylate

生成物 1

HCID 59201303(S)-tert-butyl 2,2-dimethyl-4-(((S)-tetrahydrofuran-3-yl)methyl)oxazolidine-3-carboxylate収率 67.2%

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒
HCID 8857
Ethyl Acetate
溶媒

実験手順

To a solution of (S)-tert-butyl 4-((S)-2-((tert-butyldimethylsilyloxy)methyl)-4-(methylsulfonyloxy)butyl)-2,2-dimethyloxazolidine-3-carboxylate (6.2 g) in 200 mL of THF was added TEAF. The reaction mixture was stirred for 12 h under reflux. The mixture was diluted with EA, washed with water back extracted EA. The combined organic layer was washed with brine, filtered, and concentrated. The crude product was purified by flash column to give the pure product (S)-tert-butyl 2,2-dimethyl-4-(((S)-tetrahydrofuran-3-yl)methyl)oxazolidine-3-carboxylate (2.4 g, 67%).

後処理

  1. temperatureunder reflux
  2. washwashed with water back extracted EA
  3. washThe combined organic layer was washed with brine
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude product was purified by flash column

出典と根拠

ORDレコード
ord-59ffbf98deaf4dc8aaea2b4284e0ad96
出典データセット
uspto-grants-2013_07
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08487108B2

反応ノート

読み込み中…

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