Oxygen → 3-(3-Bromophenyl)oxetane

HRID 1475788노트

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HRID 1475788 반응식
[Br:1][C:2]1[CH:3]=[C:4](B(O)O)[CH:5]=[CH:6][CH:7]=1.C[Si]([N-][Si](C)(C)C)(C)C.[Na+].Cl.N[C@@H]1CC[CH2:26][CH2:25][C@H:24]1[OH:29].O=O>CC(O)C>[Br:1][C:2]1[CH:3]=[C:4]([CH:25]2[CH2:24][O:29][CH2:26]2)[CH:5]=[CH:6][CH:7]=1

참가 물질

6

반응물 4

HCID 977OxygenHCID 2724254Sodium bis(trimethylsilyl)amideHCID 2734318(3-Bromophenyl)boronic acidHCID 12228412Cyclohexanol, 2-amino-, hydrochloride (1:1), (1R,2R)-

생성물 1

HCID 534843193-(3-Bromophenyl)oxetane수율 939.9%

시약·촉매·용매 1

HCID 3776Isopropanol용매

실험 절차

4.7 g of 3-bromophenylboronic acid, 219 mg of NiI2, 4.3 g of sodium bis(trimethylsilyl)amide, and 106 mg of trans-2-aminocyclohexanol hydrochloride were added to 14 ml of anhydrous 2-propanol and oxygen removed by passing argon through the mixture for 10 minutes. Then, a solution of 2.2 g of 3-iodo-oxetane in 1 ml of anhydrous 2-propanol was added and the mixture kept at 80° C. under microwave irradiation for 50 minutes. The mixture was then evaporated, distributed between 100 ml of water and 100 ml of EA, and the aqueous layer extracted twice using 20 ml of EA each. The organic layer was then dried using MgSO4 and evaporated. Chromatography on silica gel using EA/HEP 1:4 yielded 1.4 g of the title compound, colorless oil. Rf (EA/HEP 1:4)=0.27

후처리

  1. customremoved
  2. customfor 10 minutes
  3. additionThen, a solution of 2.2 g of 3-iodo-oxetane in 1 ml of anhydrous 2-propanol was added
  4. customthe mixture kept at 80° C. under microwave irradiation for 50 minutes
  5. customThe mixture was then evaporated
  6. extractionthe aqueous layer extracted twice
  7. customThe organic layer was then dried
  8. customevaporated

출처 및 근거

ORD 기록
ord-4a7d303081354234a32e3084b38c6142
출처 데이터셋
uspto-grants-2015_04
특허 번호
US09018383B2

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