4-Nitrobenzoic Acid → HCID 69430112, compound

HRID 1269911Notes

Reaction equation

HRID 1269911 reaction equation
[OH:1][C@@H:2]1[CH2:7][C@H:6]([N:8]2[C:16](=[O:17])[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[C:9]2=[O:18])[C:5]([CH3:20])([CH3:19])[CH2:4][CH2:3]1.[N+:21]([C:24]1[CH:32]=[CH:31][C:27]([C:28](O)=[O:29])=[CH:26][CH:25]=1)([O-:23])=[O:22].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O.C1(C)C=CC=CC=1>O1CCCC1>[N+:21]([C:24]1[CH:25]=[CH:26][C:27]([C:28]([O:1][C@H:2]2[CH2:3][CH2:4][C:5]([CH3:20])([CH3:19])[C@H:6]([N:8]3[C:16](=[O:17])[C:15]4[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=4)[C:9]3=[O:18])[CH2:7]2)=[O:29])=[CH:31][CH:32]=1)([O-:23])=[O:22]

Participants

6

Reactant 4

HCID 61084-Nitrobenzoic AcidHCID 11776TriphenylphosphineHCID 66777355Diethylazodicarboxylate tolueneHCID 69430046HCID 69430046, compound

Product 1

HCID 69430112HCID 69430112, compoundYield 114.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of the cis-2-(5-hydroxy-2,2-dimethylcyclohexyl)-1H-isoindole-1,3(2H)-dione (500 mg, 1.83 mmol) obtained in Example 590 in tetrahydrofuran (10 ml) were added 4-nitrobenzoic acid (321 mg, 1.05 mmol), triphenylphosphine (576 mg, 2.20 mmol) and a 40%-diethyl azodicarboxylate/toluene solution (1.00 ml, 2.20 mmol) at 3° C., and stirred overnight at room temperature. The reaction solution was concentrated and the resulting residue was purified by a silica gel column chromatography (eluent: hexane/ethyl acetate) to obtain trans-3-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)-4,4-dimethylcyclohexyl 4-nitrobenzoate (509 mg, 66%).

Workup

  1. concentrationThe reaction solution was concentrated
  2. customthe resulting residue was purified by a silica gel column chromatography (eluent: hexane/ethyl acetate)

Sources & evidence

ORD record
ord-f5fe72b3610f4e069368fe512fe7b4ef
Source dataset
uspto-grants-2007_04
Patent number
US07199147B2

Reaction notes

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