Phthalimide → HCID 117643186, compound

HRID 2171274Notes

Reaction equation

HRID 2171274 reaction equation
C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[C:20]1(=[O:30])[NH:24][C:23](=[O:25])[C:22]2=[CH:26][CH:27]=[CH:28][CH:29]=[C:21]12.N(C(OCC)=O)=NC(OCC)=O.[C:43]([O:47][C:48]([NH:50][CH:51]1[CH:56](O)[CH2:55][CH2:54][N:53]([C:58]([O:60][CH2:61][C:62]2[CH:67]=[CH:66][CH:65]=[CH:64][CH:63]=2)=[O:59])[CH2:52]1)=[O:49])([CH3:46])([CH3:45])[CH3:44]>O.C1COCC1>[C:43]([O:47][C:48]([NH:50][CH:51]1[CH:56]([N:24]2[C:20](=[O:30])[C:21]3[C:22](=[CH:26][CH:27]=[CH:28][CH:29]=3)[C:23]2=[O:25])[CH2:55][CH2:54][N:53]([C:58]([O:60][CH2:61][C:62]2[CH:67]=[CH:66][CH:65]=[CH:64][CH:63]=2)=[O:59])[CH2:52]1)=[O:49])([CH3:46])([CH3:44])[CH3:45]

Participants

7

Reactant 4

HCID 6809PhthalimideHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 67972312Benzyl 3-((tert-butoxycarbonyl)amino)-4-hydroxypiperidine-1-carboxylate

Product 1

HCID 117643186HCID 117643186, compoundYield 30%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

PPh3 (412 mg), phthalimide (252 mg), and diethyl azodicarboxylate (40% in toluene solution) (0.712 ml) were added to a THF (5 ml) solution containing benzyl 3-((tert-butoxycarbonyl)amino)-4-hydroxypiperidin-1-carboxylate (500 mg), followed by stirring at room temperature for 4 hours. Water was added to the reaction solution, followed by extraction with ethyl acetate. The organic layers were washed with saturated saline and dried over anhydrous sodium sulfate. The solvent was distilled away under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=9:1 to 15:7). Colorless oily matter of benzyl 3-((tert-butoxycarbonyl)amino)-4-(1,3-dioxoisoindolin-2-yl)piperidin-1-carboxylate (205 mg) was thus obtained.

Workup

  1. extractionfollowed by extraction with ethyl acetate
  2. washThe organic layers were washed with saturated saline
  3. dry with materialdried over anhydrous sodium sulfate
  4. distillationThe solvent was distilled away under reduced pressure
  5. customThe obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=9:1 to 15:7)

Sources & evidence

ORD record
ord-d66e6014d1554e4d8b1e389cffe3292d
Source dataset
uspto-grants-2015_06
Patent number
US09051310B2

Reaction notes

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