N-Hydroxyphthalimide → HCID 22861110, compound

HRID 439893Notes

Reaction equation

HRID 439893 reaction equation
N(C(OCC)=O)=NC(OCC)=O.[C:13]([NH:20][CH2:21][C@H:22]1[CH2:24][C@H:23]1[CH2:25][OH:26])([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14].O[N:28]1[C:32](=[O:33])[C:31]2=[CH:34][CH:35]=[CH:36][CH:37]=[C:30]2[C:29]1=[O:38].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1C=CC=CC=1>[C:13]([NH:20][CH2:21][C@H:22]1[CH2:24][C@H:23]1[CH2:25][O:26][N:28]1[C:32](=[O:33])[C:31]2[C:30](=[CH:37][CH:36]=[CH:35][CH:34]=2)[C:29]1=[O:38])([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14]

Participants

6

Reactant 4

HCID 10665N-HydroxyphthalimideHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 11820138HCID 11820138, compound

Product 1

HCID 22861110HCID 22861110, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Procedure

A solution of 2.61 ml (0.0157 mol) of diethyl azodicarboxylate (93%) in 15 ml of benzene is added dropwise to a mixture of 3 g (0.0149 mol) of cis-2-(N-BOC-aminomethyl)-cyclopropanemethanol, 2.43 g (0.0149 mol) of N-hydroxyphthalimide, 3.9 g (0.0149 mol) of triphenylphosphine and 120 ml of benzene at 20°-30° C., while stirring. The reaction mixture is stirred at room temperature for 16 hours and filtered, the crystalline residue is washed with benzene and the filtrate is evaporated in vacuo. The residue is purified by means of flash chromatography on silica gel using hexane and hexane/ethyl acetate (2:1). After evaporation of the product-containing fractions and crystallization of the residue from methanol/hexane, the title compound is obtained, m.p. 96°-97° C.

Workup

  1. stirringThe reaction mixture is stirred at room temperature for 16 hours
  2. filtrationfiltered
  3. washthe crystalline residue is washed with benzene
  4. customthe filtrate is evaporated in vacuo
  5. customThe residue is purified by means of flash chromatography on silica gel
  6. customAfter evaporation of the product-containing fractions and crystallization of the residue from methanol/hexane

Sources & evidence

ORD record
ord-5d6b424caee3460888f1785817ac7572
Source dataset
uspto-grants-1996_05
Patent number
US05516806

Reaction notes

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