Phthalimide → HCID 20468458, compound

HRID 1903246Notes

Reaction equation

HRID 1903246 reaction equation
N(C(OCC)=O)=NC(OCC)=O.[F:13][CH:14]([F:27])[CH:15]([NH:19][CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[CH2:16][CH2:17]O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:47]1(=[O:57])[NH:51][C:50](=[O:52])[C:49]2=[CH:53][CH:54]=[CH:55][CH:56]=[C:48]12>O1CCCC1.C(OCC)(=O)C.C1CCCCC1>[F:13][CH:14]([F:27])[CH:15]([NH:19][CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[CH2:16][CH2:17][N:51]1[C:50](=[O:52])[C:49]2=[CH:53][CH:54]=[CH:55][CH:56]=[C:48]2[C:47]1=[O:57]

Participants

7

Reactant 4

HCID 6809PhthalimideHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 204684403-(Benzylamino)-4,4-difluorobutan-1-ol

Product 1

HCID 20468458HCID 20468458, compoundYield 65%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 21867204Cyclohexane ethylacetateSolvent

Procedure

A solution of diethyl azodicarboxylate (0.639 g, 3.65 mM), in anhydrous tetrahydrofuran (5 ml) is added, dropwise, over a period of 0.5 hours, at room temperature to a mixture of 4,4-difluoro-3-benzylamino-butanol (0.790 g, 3.65 mM) prepared as in Step C, triphenylphosphine (0.962 g, 3.65 mM), and phthalimide (0.540 g, 3.65 mM) in tetrahydrofuran (20 ml). After stirring for 2.5 hours at room temperature, the solvent is evaporated in vacuo. The residue is taken off in benzene and the solution filtered. The solid is washed three time with benzene. The filtrate is evaporated to dryness; the residue is taken off in diethyl ether. Filtration and evaporation of the solvent in vacuo yields a yellow oil. The expected phthalimide is isolated by column chromatography (medium pressure silica gel chromatography technique, ethyl acetate/cyclohexane 2:8): 0.800 g (yield 65%).

Workup

  1. customthe solvent is evaporated in vacuo
  2. filtrationthe solution filtered
  3. washThe solid is washed three time with benzene
  4. customThe filtrate is evaporated to dryness
  5. filtrationFiltration and evaporation of the solvent in vacuo
  6. customyields a yellow oil

Sources & evidence

ORD record
ord-bc961804a5bb49fe8baa0076d3db5c30
Source dataset
uspto-grants-1984_03
Patent number
US04435425

Reaction notes

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