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

HRID 2172005Notes

Reaction equation

HRID 2172005 reaction equation
[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

Participants

6

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-a34738a2d6dc4e64941217b9a713a7ee
Source dataset
uspto-grants-2015_06
Patent number
US09051321B2

Reaction notes

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