Potassium tert-butoxide → (S)-tert-butyl 4-(1-cyclopropylvinyl)-2,2-dimethyloxazolidine-3-carboxylate

HRID 627243ノート

反応式

HRID 627243 の反応式
[CH3:1]C(C)([O-])C.[K+].[CH:7]1([C:10]([C@H:12]2[CH2:16][O:15][C:14]([CH3:18])([CH3:17])[N:13]2[C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])=O)[CH2:9][CH2:8]1>CCOCC.[Br-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH:7]1([C:10]([C@H:12]2[CH2:16][O:15][C:14]([CH3:18])([CH3:17])[N:13]2[C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])=[CH2:1])[CH2:9][CH2:8]1

参加物

5

反応物 2

HCID 23665647Potassium tert-butoxideHCID 89851368(R)-tert-butyl 4-(cyclopropanecarbonyl)-2,2-dimethyloxazolidine-3-carboxylate2 回

生成物 1

HCID 89851406(S)-tert-butyl 4-(1-cyclopropylvinyl)-2,2-dimethyloxazolidine-3-carboxylate収率 89%

試薬・触媒・溶媒 2

HCID 74505Methyltriphenyliphosphonium bromide触媒HCID 3283Diethyl Ether溶媒2 回

反応条件

温度
40 °C

実験手順

To a suspension of potassium tert-butoxide (9.29 g, 82.80 mmol) in ether (250 mL) at room temperature was added methyltriphenylphosphonium bromide (29.6 g, 82.80 mmol). The mixture turned bright yellow and was heated to 40° C. for 1 hour. The mixture was cooled to room temperature and a solution of (R)-tert-butyl 4-(cyclopropanecarbonyl)-2,2-dimethyloxazolidine-3-carboxylate (Intermediate 231, 11.15 g, 41.40 mmol) in ether (30 mL) was added and the reaction mixture was stirred for 2 hours. The reaction was quenched with water (10 mL) and the layers were separated. The aqueous was extracted once with ether. The combined organic extracts were dried over magnesium sulfate, filtered and concentrated. Silica gel chromatography (0%-15% ethyl acetate/hexanes) afforded the title compound as a colorless oil (9.84 g, 89%).

後処理

  1. temperatureThe mixture was cooled to room temperature
  2. customThe reaction was quenched with water (10 mL)
  3. customthe layers were separated
  4. extractionThe aqueous was extracted once with ether
  5. dry with materialThe combined organic extracts were dried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated

出典と根拠

ORDレコード
ord-fe83ffc1e1f14c449de4c09114f90389
出典データセット
uspto-grants-2016_04
特許番号
US09309245B2

反応ノート

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