Methyl iodide → HCID 59020123, 화합물

HRID 971148노트

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HRID 971148 반응식
[C:1]([O:5][C:6](=[O:18])[NH:7][C:8]1([C:11]2[CH:16]=[CH:15][C:14]([I:17])=[CH:13][CH:12]=2)[CH2:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2].CI.[H-].[Na+].[CH3:23]COC(C)=O>C1COCC1.O>[C:1]([O:5][C:6](=[O:18])[N:7]([C:8]1([C:11]2[CH:12]=[CH:13][C:14]([I:17])=[CH:15][CH:16]=2)[CH2:9][CH2:10]1)[CH3:23])([CH3:4])([CH3:2])[CH3:3]

참가 물질

7

반응물 4

HCID 6328Methyl iodideHCID 8857Ethyl AcetateHCID 24758Sodium hydrideHCID 59019959tert-Butyl (1-(4-iodophenyl)cyclopropyl)carbamate

생성물 1

HCID 59020123HCID 59020123, 화합물수율 95%

시약·촉매·용매 2

HCID 962Water촉매HCID 8028Tetrahydrofuran용매

실험 절차

Part A. 1-(4-Iodophenyl)cyclopropyl-carbamic acid tert-butyl ester (2.14 g, 5.85 mmol) was stirred in THF (20 mL) at 0° C. under N2. MeI (3 mL) was added followed by portionwise addition of NaH (2.34 g, 5 eq). The reaction was stirred at rt overnight. Several drops of H2O and EtOAc (20 mL) were added to quench the reaction. The organic solvent was evaporated, and H2O was added. It was extracted with Et2O (2×), washed with brine, dried over MgSO4, and concentrated to dryness. The residue was purified by FCC (silica gel, CH2Cl2:hexanes=0:1 to 1:1 to 1:0) to give pure [1-(4-iodophenyl)cyclopropyl]-methyl-carbamic acid tert-butyl ester as a white solid (2.07 g, yield 95%). LC/MS (ESI+) 373.8 (M+H), tR=2.95 min (10–90% CH3CN in H2O in a 4-min run).

후처리

  1. customto quench
  2. customthe reaction
  3. customThe organic solvent was evaporated
  4. additionH2O was added
  5. extractionIt was extracted with Et2O (2×)
  6. washwashed with brine
  7. dry with materialdried over MgSO4
  8. concentrationconcentrated to dryness
  9. customThe residue was purified by FCC (silica gel, CH2Cl2:hexanes=0:1 to 1:1 to 1:0)

출처 및 근거

ORD 기록
ord-a401d52b00ca4ee092edf6dc12659914
출처 데이터셋
uspto-grants-2007_12
특허 번호
US07312214B2

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