Phthalimide → HCID 117839941, compound

HRID 1477640Notes

Reaction equation

HRID 1477640 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13](O)[CH2:12][N:11]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:10][CH:9]=2)=[CH:4][CH:3]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:41]1(=[O:51])[NH:45][C:44](=[O:46])[C:43]2=[CH:47][CH:48]=[CH:49][CH:50]=[C:42]12.N(C(OC(C)C)=O)=NC(OC(C)C)=O>O1CCCC1>[O:46]=[C:44]1[C:43]2[C:42](=[CH:50][CH:49]=[CH:48][CH:47]=2)[C:41](=[O:51])[N:45]1[CH:13]1[CH2:12][N:11]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:10][CH:9]=[C:8]1[C:5]1[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=1

Participants

6

Reactant 4

HCID 6809PhthalimideHCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 117839697HCID 117839697, compound

Product 1

HCID 117839941HCID 117839941, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a tetrahydrofuran solution (10 mL) of tert-butyl 4-(4-fluorophenyl)-5-hydroxy-5,6-dihydropyridine-1(2H)-carboxylate (1.00 g, 3.41 mmol) synthesized in Reference Synthesis Example 354, triphenylphosphine (0.894 g, 3.41 mmol), and phthalimide (0.501 g, 3.41 mmol), diisopropyl azodicarboxylate (1.9 M, toluene solution) (1.97 mL, 3.75 mmol) was added dropwise and the resultant mixture was stirred at room temperature for 1 day. After completion of the reaction, the reaction solution was concentrated and the resultant residue was purified by silica gel column chromatography to obtain the title compound (1.21 g, yield 84%).

Workup

  1. additionwas added dropwise
  2. customAfter completion of the reaction
  3. concentrationthe reaction solution was concentrated
  4. customthe resultant residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-5a18fe8932b94e64a6ea8e5c73316aa3
Source dataset
uspto-grants-2016_08
Patent number
US09403798B2

Reaction notes

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