1-(Diphenylmethyl)azetidin-3-ol → 1-(Diphenylmethyl)-3-[(2-methylprop-2-en-1-yl)oxy]azetidine

HRID 2172005노트

반응식

HRID 2172005 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.[CH3:19][C:20]([O-])([CH3:22])[CH3:21].[K+].BrCC(C)=C>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][CH2:21][C:20]([CH3:22])=[CH2:19])[CH2:9]2)[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

참가 물질

6

반응물 3

HCID 3304481-(Diphenylmethyl)azetidin-3-olHCID 3577853-Bromo-2-methyl-1-propeneHCID 23665647Potassium tert-butoxide

생성물 1

HCID 671545541-(Diphenylmethyl)-3-[(2-methylprop-2-en-1-yl)oxy]azetidine수율 94%

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매

실험 절차

A solution of 1-diphenylmethylazetidin-3-ol (239 mg, 1.0 mmol) in THF (3.6 mL) was cooled to 0° C. t-BuOK (1M in THF, 3.6 mL) was added dropwise and the reaction mixture was stirred at room temperature for 1 h then cooled to 0° C. 3-Bromo-2-methyl-1-propene (504 μL, 5.0 mmol) was added and the solution was stirred from 0° C. to room temperature overnight. The reaction mixture was diluted with H2O and extracted twice with EtOAc. The organic layers were combined, dried over Na2SO4 and concentrated to dryness to give the title compound (276 mg, 94%) as a yellow oil.

후처리

  1. additionwas added dropwise
  2. temperaturethen cooled to 0° C
  3. stirringthe solution was stirred from 0° C. to room temperature overnight
  4. extractionextracted twice with EtOAc
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated to dryness

출처 및 근거

ORD 기록
ord-a34738a2d6dc4e64941217b9a713a7ee
출처 데이터셋
uspto-grants-2015_06
특허 번호
US09051321B2

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