1-Iodopentane → 1-(Diphenylmethyl)-3-(pentyloxy)azetidine

HRID 2171993

반응식

HRID 2171993 반응식
[C:1]1([CH:7]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[N:8]2[CH2:11][CH:10]([OH:12])[CH2:9]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CC([O-])(C)C.[K+].I[CH2:26][CH2:27][CH2:28][CH2:29][CH3:30]>C1COCC1.O>[C:13]1([CH:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[N:8]2[CH2:11][CH:10]([O:12][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30])[CH2:9]2)[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

참가 물질

6

반응물 3

HCID 123351-IodopentaneHCID 3304481-(Diphenylmethyl)azetidin-3-olHCID 23665647Potassium tert-butoxide

생성물 1

HCID 671545431-(Diphenylmethyl)-3-(pentyloxy)azetidine수율 69%

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매

실험 절차

A solution of 1-diphenylmethylazetidin-3-ol (300 mg, 1.25 mmol) in THF (4.5 mL) was cooled to 0° C. t-BuOK (1M in THF, 3.75 mL) was added dropwise and the reaction mixture was stirred at room temperature for 1 h then cooled to 0° C. 1-Iodopentane (816 μL, 6.25 mmol) was added and the solution was stirred at room temperature for 18 h. The reaction mixture was diluted with H2O and extracted twice with EtOAc. The organic layers were combined, dried over Na2SO4 and concentrated to dryness. The residue was purified on column chromatography (eluent: pentane/EtOAc, 95/5) to give the title compound (267 mg, 69%) as a clear oil.

후처리

  1. additionwas added dropwise
  2. temperaturethen cooled to 0° C
  3. stirringthe solution was stirred at room temperature for 18 h
  4. extractionextracted twice with EtOAc
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated to dryness
  7. customThe residue was purified on column chromatography (eluent: pentane/EtOAc, 95/5)

출처 및 근거

ORD 기록
ord-18859e32661c4f8e93a07df7028880b5
출처 데이터셋
uspto-grants-2015_06
특허 번호
US09051321B2

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