Benzophenone → HCID 117697623, compound

HRID 1778480Notes

Reaction equation

HRID 1778480 reaction equation
[C:1]([N:9]([CH2:16][C:17]([F:19])=[CH2:18])[C:10](=[CH2:15])[C:11]([O:13][CH3:14])=[O:12])(=O)C1C=CC=CC=1.C(C1C=CC=CC=1)(=O)C.C(C1C=CC=CC=1)(=O)C1C=CC=CC=1>C1C=CC=CC=1>[F:19][C:17]12[CH2:15][C:10]([C:11]([O:13][CH3:14])=[O:12])([CH2:18]1)[N:9]([CH3:1])[CH2:16]2

Participants

5

Reactant 3

HCID 3102BenzophenoneHCID 7410AcetophenoneHCID 102173134HCID 102173134, compound

Product 1

HCID 117697623HCID 117697623, compoundYield 63.4%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

Methyl 2-[benzoyl(2-fluoroallyl)amino]prop-2-enoate (AR3) (380 mg, 1.44 mmol), acetophenone (30 mg), benzophenone (40 mg) were dissolved in 25 mL of benzene. The solution formed was irradiated in a quartz reactor by 500 W medium pressure mercury lamp at room temperature for 10 hours. The reaction mixture was concentrated, and the residue was purified by flash column chromatography (hexane/EtOAc=3/1) to give methyl 1-fluoro-3-methyl-3-azabicyclo[2.1.1]hexane-4-carboxylate (AR4) (240 mg, 0.913 mmol, 63%). LC/MS: calc'd 264 (MH+), exp 264 (MH+).

Workup

  1. customThe solution formed
  2. customwas irradiated in a quartz reactor by 500 W medium pressure mercury lamp at room temperature for 10 hours
  3. concentrationThe reaction mixture was concentrated
  4. customthe residue was purified by flash column chromatography (hexane/EtOAc=3/1)

Sources & evidence

ORD record
ord-71f2ffc43ec5419193ccd0b693aa2f06
Source dataset
uspto-grants-2016_02
Patent number
US09266904B2

Reaction notes

Loading…