N-Carbethoxyphthalimide → 3-Phthalimido-4,4-difluoro-7-methoxy-1-heptene

HRID 568984Notes

Reaction equation

HRID 568984 reaction equation
[NH2:1][CH:2]([C:5]([F:12])([F:11])[CH2:6][CH2:7][CH2:8][O:9][CH3:10])[CH:3]=[CH2:4].C(N1[C:22](=[O:23])[C:21]2=[CH:24][CH:25]=[CH:26][CH:27]=[C:20]2[C:19]1=[O:28])(OCC)=O>C1C=CC=CC=1>[C:19]1(=[O:28])[N:1]([CH:2]([C:5]([F:11])([F:12])[CH2:6][CH2:7][CH2:8][O:9][CH3:10])[CH:3]=[CH2:4])[C:22](=[O:23])[C:21]2=[CH:24][CH:25]=[CH:26][CH:27]=[C:20]12

Participants

4

Reactant 2

HCID 31187N-CarbethoxyphthalimideHCID 201494503-Amino-4,4-difluoro-7-methoxy-1-heptene

Product 1

HCID 201495083-Phthalimido-4,4-difluoro-7-methoxy-1-hepteneYield 85.7%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A mixture of 3-amino-4,4-difluoro-7-methoxy-1-heptene (420 mg, 2.3 mmoles) and N-carbetoxyphthalimide (506 mg, 2.3 mmoles) in benzene (9 ml) is kept at 25° C. overnight. After concentration under reduced pressure, the residue is dissolved in dichloromethane (5 ml) and treated with triethylamine (0.7 ml) for 41/2 hours. After addition of dichloromethane, the solution is washed with 1N HCl and water. Usual work-up affords an oil (610 mg) which is purified by chromatography on silica (ethyl acetate/petroleum ether: 20/80 RF: 0.4): 440 mg (62%).

Workup

  1. concentrationAfter concentration under reduced pressure
  2. dissolutionthe residue is dissolved in dichloromethane (5 ml)
  3. additiontreated with triethylamine (0.7 ml) for 41/2 hours
  4. additionAfter addition of dichloromethane
  5. washthe solution is washed with 1N HCl and water

Sources & evidence

ORD record
ord-96c2a1ef70c84a0986a85f3856c8c4ee
Source dataset
uspto-grants-1988_03
Patent number
US04730006

Reaction notes

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