3-Bromo-2-methyl-1-propene → HCID 178441184, 화합물

HRID 2360286

반응식

HRID 2360286 반응식
[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

참가 물질

5

반응물 3

HCID 3577853-Bromo-2-methyl-1-propeneHCID 2724682Lithium diisopropylamideHCID 178518180HCID 178518180, 화합물

생성물 1

HCID 178441184HCID 178441184, 화합물

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
-78 °C

실험 절차

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)+.

후처리

  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)

출처 및 근거

ORD 기록
ord-b7dd2c3c2757432280f485cab6696c81
출처 데이터셋
uspto-grants-2014_04
특허 번호
US08686011B2

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