Ethyl Acetate → HCID 22884192, compound

HRID 1598380Notes

Reaction equation

HRID 1598380 reaction equation
[CH2:1]([O:3][C:4]([N:6]([CH2:15][C@H:16]1[O:21][C@@H:20]([CH2:22]I)[CH2:19][CH2:18][CH2:17]1)[CH2:7][C:8]1[CH:13]=[CH:12][C:11]([F:14])=[CH:10][CH:9]=1)=[O:5])[CH3:2].[C:24]1(=[O:34])[NH:28][C:27](=[O:29])[C:26]2=[CH:30][CH:31]=[CH:32][CH:33]=[C:25]12.[K].C(OCC)(=O)C>CN(C)C=O>[CH2:1]([O:3][C:4]([N:6]([CH2:15][C@H:16]1[O:21][C@@H:20]([CH2:22][N:28]2[C:27](=[O:29])[C:26]3=[CH:30][CH:31]=[CH:32][CH:33]=[C:25]3[C:24]2=[O:34])[CH2:19][CH2:18][CH2:17]1)[CH2:7][C:8]1[CH:13]=[CH:12][C:11]([F:14])=[CH:10][CH:9]=1)=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 22884191HCID 22884191, compoundHCID 24194345Phthalimide potassium salt

Product 1

HCID 22884192HCID 22884192, compoundYield 202.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of cis-6-[N-ethoxycarbonyl-N-(p-fluorobenzyl)aminomethyl]-2-iodomethyltetrahydropyrane (2.71 g, 5.10 mmol) in dimethylformamide (30 ml) was added potassium phthalimide (1.04 g, 5.61 mmol) and the mixture was stirred at 100° C. for 10 hours. To the reaction mixture was added ethyl acetate (200 ml), washed successively with purified water (50 ml) and saturated aqueous sodium chloride (50 ml), dried over anhydrous magnesium sulfate and the solvent was distilled off under reduced pressure to give crude cis-6-[N-ethoxycarbonyl-N-(p-fluorobenzyl)aminomethyl]-2-phthalimidomethyltetrahydropyrane (4.69 g). This compound was used for the subsequent reaction without purification.

Workup

  1. washwashed successively with purified water (50 ml) and saturated aqueous sodium chloride (50 ml)
  2. dry with materialdried over anhydrous magnesium sulfate
  3. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-3f443cb24cce42ca84b5c58e78e94931
Source dataset
uspto-grants-1998_04
Patent number
US05736550

Reaction notes

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