N-Hydroxyphthalimide → HCID 67823577, compound

HRID 1109761Notes

Reaction equation

HRID 1109761 reaction equation
N(C(OCC)=O)=NC(OCC)=O.[C:13]([N:20]1[CH2:25][CH2:24][C@H:23]([OH:26])[CH2:22][C@@H:21]1[CH2:27][CH3:28])([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14].O[N:30]1[C:34](=[O:35])[C:33]2=[CH:36][CH:37]=[CH:38][CH:39]=[C:32]2[C:31]1=[O:40].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1C=CC=CC=1>[C:13]([N:20]1[CH2:25][CH2:24][C@@H:23]([O:26][N:30]2[C:34](=[O:35])[C:33]3[C:32](=[CH:39][CH:38]=[CH:37][CH:36]=3)[C:31]2=[O:40])[CH2:22][C@@H:21]1[CH2:27][CH3:28])([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14]

Participants

6

Reactant 4

HCID 10665N-HydroxyphthalimideHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 67823323HCID 67823323, compound

Product 1

HCID 67823577HCID 67823577, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Procedure

With stirring and under nitrogen, a solution of 0.283 ml (0.001693 mol) of diethyl azodicarboxylate (93%) in 1 ml of benzene is added dropwise at 20°-30° C. to a suspension of 0.37 g (0.001613 mol) of cis-N-BOC-2-ethyl-4-hydroxypiperidine, 0.263 g (0.001613 mol) of N-hydroxyphthalimide and 0.423 g (0.001613 mol) of triphenylphosphine in 5 ml of benzene. The reaction mixture is further stirred for 15 hours at room temperature, then filtered to remove precipitated diethyl 1,2-hydrazinedicarboxylate, and the filtrate is concentrated under vacuum. The residue is purified by flash chromatography over silica gel using ethyl acetate:hexane (1:3), to give the title compound as a colourless resin; Rf =0.66 (silica gel/ethyl acetate:hexane (2:1)).

Workup

  1. stirringThe reaction mixture is further stirred for 15 hours at room temperature
  2. filtrationfiltered
  3. customto remove
  4. customprecipitated diethyl 1,2-hydrazinedicarboxylate
  5. concentrationthe filtrate is concentrated under vacuum
  6. customThe residue is purified by flash chromatography over silica gel

Sources & evidence

ORD record
ord-81b7878b1e8241808334282dc978955d
Source dataset
uspto-grants-1994_06
Patent number
US05322852

Reaction notes

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