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

HRID 451826
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HRID 451826 반응식
[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
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참가 물질

5

반응물 2

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

생성물 1

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

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매
HCID 8857
Ethyl Acetate
용매

실험 절차

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%).

후처리

  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

출처 및 근거

ORD 기록
ord-59ffbf98deaf4dc8aaea2b4284e0ad96
출처 데이터셋
uspto-grants-2013_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08487108B2

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