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

HRID 82937

Reaction equation

HRID 82937 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.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

Participants

6

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-35b2cff55e0f4482aa43c358dd7db91b
Source dataset
uspto-grants-2014_09
Patent number
US08846711B2

Linked notes

Loading…