Phthalimide → HCID 69101410, compound

HRID 2222571Notes

Reaction equation

HRID 2222571 reaction equation
O[CH:2]([C:23]1[CH:28]=[CH:27]N=CC=1)[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][N:12]1[C:16](=[O:17])[C:15]2=[CH:18][CH:19]=[CH:20][CH:21]=[C:14]2[C:13]1=[O:22].[C:29]1(=[O:39])[NH:33][C:32](=[O:34])[C:31]2=[CH:35][CH:36]=[CH:37][CH:38]=[C:30]12.C1(P([C:53]2[CH:58]=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[N:59](C(OC(C)C)=O)=NC(OC(C)C)=O>C1COCC1>[C:29]1(=[O:39])[N:33]([CH:2]([C:23]2[CH:28]=[CH:27][CH:53]=[CH:58][N:59]=2)[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][N:12]2[C:13](=[O:22])[C:14]3=[CH:21][CH:20]=[CH:19][CH:18]=[C:15]3[C:16]2=[O:17])[C:32](=[O:34])[C:31]2=[CH:35][CH:36]=[CH:37][CH:38]=[C:30]12

Participants

6

Reactant 4

HCID 6809PhthalimideHCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 69101330HCID 69101330, compound

Product 1

HCID 69101410HCID 69101410, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

1-Hydroxy-1-(4-pyridinyl)-10-phthalimidodecane (1 equiv.) is dissolved in THF with stirring. Phthalimide (1.5 equiv.) and triphenylphosphine (2.1 equiv.) are added to the solution and the resulting mixture is cooled to 0° C. Diisopropyl azodicarboxylate (2.0 equiv.) is added dropwise to the above solution and the reaction is stirred until completion. The resulting solid is filtered off and the filtrate is concentrated in vacuo. The crude product is purified by silica gel chromatography to yield 1,10-diphthalimido-1-pyridinyldecane.

Workup

  1. stirringthe reaction is stirred until completion
  2. filtrationThe resulting solid is filtered off
  3. concentrationthe filtrate is concentrated in vacuo
  4. customThe crude product is purified by silica gel chromatography

Sources & evidence

ORD record
ord-dd6ab1e0005e4e95bdbf69c8cae1f66a
Source dataset
uspto-grants-2008_05
Patent number
US07371852B2

Reaction notes

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