3-Bromo-2-methyl-1-propene → HCID 178441184、化合物

HRID 2360286

反応式

HRID 2360286 の反応式
[C@@H:1]12[CH2:7][C@@H:4]([CH2:5][CH2:6]1)[CH2:3][C@@H:2]2[NH:8][C:9]1[S:10][CH:11]([CH2:15][CH2:16][O:17][CH:18]2[CH2:23][CH2:22][CH2:21][CH2:20][O:19]2)[C:12](=[O:14])[N:13]=1.[Li+].CC([N-]C(C)C)C.Br[CH2:33][C:34]([CH3:36])=[CH2:35]>C1COCC1>[C@@H:1]12[CH2:7][C@@H:4]([CH2:5][CH2:6]1)[CH2:3][C@@H:2]2[NH:8][C:9]1[S:10][C:11]([CH2:35][C:34]([CH3:36])=[CH2:33])([CH2:15][CH2:16][O:17][CH:18]2[CH2:23][CH2:22][CH2:21][CH2:20][O:19]2)[C:12](=[O:14])[N:13]=1

参加物

5

反応物 3

HCID 3577853-Bromo-2-methyl-1-propeneHCID 2724682Lithium diisopropylamideHCID 178518180HCID 178518180、化合物

生成物 1

HCID 178441184HCID 178441184、化合物

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
-78 °C

実験手順

To the mixture of 2-((1S,2S,4R)-bicyclo[2.2.1]heptan-2-ylamino)-5-(2-(tetrahydro-2H-pyran-2-yloxy)ethyl)thiazol-4(5H)-one (1160 mg, 3.43 mmol) in THF (8.0 mL) cooled in a −78° C. bath was added LDA (2.0 M, 17.15 mL). The resulting mixture was stirred for 10 min at −78° C., and then 3-bromo-2-methylprop-1-ene (1.6 ml, 17.15 mmol) was added. After the reaction mixture was allowed to warm to room temperature and stirred ca. 18 h. Saturated NaH2PO4 was added, and the aqueous phase was extracted with EtOAc. The organic layer was washed with sat'd NH4Cl, dried over MgSO4, filtered, and concentrated in vacuo. The crude residue was purified by flash chromatography (4:1; Hexane:EtOAc) to give the title compound as yellow oil. MS (ES+): 393 (M+H)+.

後処理

  1. temperatureto warm to room temperature
  2. stirringstirred ca. 18 h
  3. extractionthe aqueous phase was extracted with EtOAc
  4. washThe organic layer was washed with sat'd NH4Cl
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe crude residue was purified by flash chromatography (4:1; Hexane:EtOAc)

出典と根拠

ORDレコード
ord-b7dd2c3c2757432280f485cab6696c81
出典データセット
uspto-grants-2014_04
特許番号
US08686011B2

関連ノート

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