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1-Bromo-3-methylbutane → HCID 70976045, 화합물

HRID 455278
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HRID 455278 반응식
[OH:1][C@@H:2]1[CH2:22][N:5]2[C:6](=[O:21])[N:7]([C:9]3[CH:14]=[CH:13][C:12]([O:15][CH2:16][C:17]([F:20])([F:19])[F:18])=[CH:11][CH:10]=3)[CH2:8][C@H:4]2[CH2:3]1.[H-].[Na+].Br[CH2:26][CH2:27][CH:28]([CH3:30])[CH3:29]>C1COCC1>[CH3:29][CH:28]([CH3:30])[CH2:27][CH2:26][O:1][C@@H:2]1[CH2:22][N:5]2[C:6](=[O:21])[N:7]([C:9]3[CH:10]=[CH:11][C:12]([O:15][CH2:16][C:17]([F:20])([F:18])[F:19])=[CH:13][CH:14]=3)[CH2:8][C@H:4]2[CH2:3]1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 3

HCID 78911-Bromo-3-methylbutaneHCID 24758Sodium hydrideHCID 70976202HCID 70976202, 화합물

생성물 1

HCID 70976045HCID 70976045, 화합물수율 49.1%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of (6S,7aR)-6-Hydroxy-2-[4-(2,2,2-trifluoro-ethoxy)-phenyl]-hexahydro-pyrrolo[1,2-c]imidazol-3-one (100 mg, 0.316 mmol) in THF (3 mL) was added NaH (60% dispersion, 18.96 mg, 0.474 mmol) at room temperature and stirred for 30 min and then added 1-Bromo-3-methyl-butane (57.3 mg, 0.379 mmol) and left stirring for 12 h. The reaction mixture was quenched with NH4Cl aq., DCM was added. The organic layer was separated, washed with water and brine, dried over Na2SO4 and concentrated. The residue was purified through column chromatography (elution with ethyl acetate in hexane) to afford 60 mg (49%) of the title compound. LC-MS: 386 [M+1]+.

후처리

  1. stirringstirring for 12 h
  2. customThe reaction mixture was quenched with NH4Cl aq., DCM
  3. additionwas added
  4. customThe organic layer was separated
  5. washwashed with water and brine
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated
  8. customThe residue was purified through column chromatography (elution with ethyl acetate in hexane)

출처 및 근거

ORD 기록
ord-a7a47296c58a4495a9b874f49ba3cc68
출처 데이터셋
uspto-grants-2013_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08497288B2

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