Water → HCID 67466423, 화합물

HRID 2202784노트

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HRID 2202784 반응식
C([Li])(C)(C)C.I[C:7]1[CH:12]=[N:11][CH:10]=[CH:9][N:8]=1.[CH2:13]([N:20]1[CH:25]2[CH2:26][CH2:27][CH:21]1[CH2:22][C:23](=[O:28])[CH2:24]2)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.O>C(OCC)C.C(OCC)(=O)C>[CH2:13]([N:20]1[CH:21]2[CH2:27][CH2:26][CH:25]1[CH2:24][C:23]([C:7]1[CH:12]=[N:11][CH:10]=[CH:9][N:8]=1)([OH:28])[CH2:22]2)[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

참가 물질

7

반응물 4

HCID 962WaterHCID 1198468-Benzyl-8-azabicyclo(3.2.1)octan-3-oneHCID 642841IodopyrazineHCID 178418306HCID 178418306, 화합물

생성물 1

HCID 67466423HCID 67466423, 화합물수율 23.1%

시약·촉매·용매 2

HCID 3283Diethyl Ether용매2회HCID 8857Ethyl Acetate용매

실험 절차

t-Butyl lithium (1.7 M, 1.18 mL, 2.00 mmol) was added dropwise to a solution of 2-iodopyrazine (0.1 mL, 1.0 mmol) in diethyl ether (10 mL) at −78° C. under nitrogen and stirred for 30 minutes. A solution of 8-benzyl-8-aza-bicyclo[3.2.1]octan-3-one (0.19 g, 0.88 mmol) in diethyl ether (5 mL) was added dropwise and stirred at −78° C. for 1 hour. It was warmed to room temperature, water and ethyl acetate were added, the organics separated, dried over sodium sulphate, filtered and the solvent removed by evaporation under vacuum. The residue was purified by flash chromatography on silica eluting with 1:1 ethyl acetate/cyclohexane. The fractions containing the desired product were concentrated under vacuum to give the title compound (0.06 g). LCMS m/z 296.3 [M+H]+. R.T.=1.97 min (Analytical Method 3).

후처리

  1. stirringstirred at −78° C. for 1 hour
  2. dry with materialthe organics separated, dried over sodium sulphate
  3. filtrationfiltered
  4. customthe solvent removed by evaporation under vacuum
  5. customThe residue was purified by flash chromatography on silica eluting with 1:1 ethyl acetate/cyclohexane
  6. additionThe fractions containing the desired product
  7. concentrationwere concentrated under vacuum

출처 및 근거

ORD 기록
ord-7b91c0e20ba54bc3a34b22fb4573e5b2
출처 데이터셋
uspto-grants-2016_06
특허 번호
US09365564B2

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