N-Hydroxyphthalimide → HCID 178475039, compound

HRID 439894Notes

Reaction equation

HRID 439894 reaction equation
N(C(OCC)=O)=NC(OCC)=O.[NH:13]([C@@H:17]1[CH2:22][CH2:21][C@H:20]([OH:23])[CH2:19][CH2:18]1)[C:14]([CH3:16])=[O:15].O[N:25]1[C:29](=[O:30])[C:28]2=[CH:31][CH:32]=[CH:33][CH:34]=[C:27]2[C:26]1=[O:35].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>O1CCCC1>[NH:13]([C@H:17]1[CH2:22][CH2:21][C@H:20]([O:23][N:25]2[C:29](=[O:30])[C:28]3[C:27](=[CH:34][CH:33]=[CH:32][CH:31]=3)[C:26]2=[O:35])[CH2:19][CH2:18]1)[C:14]([CH3:16])=[O:15]

Participants

6

Reactant 4

HCID 10665N-HydroxyphthalimideHCID 11776Triphenylphosphine2×HCID 220568ethyl N-ethoxycarbonyliminocarbamate2×HCID 178475037HCID 178475037, compound

Product 1

HCID 178475039HCID 178475039, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 39.5 ml (0.2413 mol) of diethyl azodicarboxylate (95%) in 300 ml of tetrahydrofuran is added dropwise to a mixture of 36.13 g (0.2298 mol) of cis-4-acetaminocyclohexanol [Ber. Dtsch. Chem. Ges. 72, 995 (1939)], 37.49 g (0.2298 mol) of N-hydroxyphthalimide, 60.28 g of triphenylphosphine and 1500 ml of tetrahydrofuran at 20°-30° C., while stirring. After stirring at room temperature for 14 hours, in each case 20% of the amount of triphenylphosphine and diethyl azodicarboxylate originally employed is again added to the reaction mixture, stirring is continued for 6 hours and the reaction mixture is left to stand at room temperature for 2.5 days. The crystalline precipitate formed is filtered off and washed with tetrahydrofuran. The title compound thus obtained melts at 210°-213° C. The yield can be increased by further recrystallization or chromatography of the mother liquor.

Workup

  1. additionoriginally employed is again added to the reaction mixture
  2. stirringstirring
  3. waitthe reaction mixture is left
  4. waitto stand at room temperature for 2.5 days
  5. customThe crystalline precipitate formed
  6. filtrationis filtered off
  7. washwashed with tetrahydrofuran
  8. customThe yield can
  9. temperaturebe increased by further recrystallization or chromatography of the mother liquor

Sources & evidence

ORD record
ord-a9aed1bd500f480faa45c00fa26a3a62
Source dataset
uspto-grants-1996_05
Patent number
US05516806

Reaction notes

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