Phthalimide → Ethyl 4-(1,3-dioxoisoindolin-2-yl)-1-methylcyclohexanecarboxylate

HRID 1944720Notes

Reaction equation

HRID 1944720 reaction equation
O[CH:2]1[CH2:7][CH2:6][C:5]([CH3:13])([C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH2:4][CH2:3]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:33]1(=[O:43])[NH:37][C:36](=[O:38])[C:35]2=[CH:39][CH:40]=[CH:41][CH:42]=[C:34]12.CC(OC(/N=N/C(OC(C)C)=O)=O)C>C1COCC1>[O:38]=[C:36]1[C:35]2[C:34](=[CH:42][CH:41]=[CH:40][CH:39]=2)[C:33](=[O:43])[N:37]1[CH:2]1[CH2:7][CH2:6][C:5]([CH3:13])([C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH2:4][CH2:3]1

Participants

6

Reactant 4

HCID 6809PhthalimideHCID 11776TriphenylphosphineHCID 5363146Diisopropyl azodicarboxylateHCID 58230927Ethyl 4-hydroxy-1-methylcyclohexanecarboxylate2×

Product 1

HCID 58074352Ethyl 4-(1,3-dioxoisoindolin-2-yl)-1-methylcyclohexanecarboxylateYield 63.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Ethyl 4-hydroxy-1-methylcyclohexanecarboxylate (Intermediate 67, 930 mg, 4.99 mmol), triphenylphosphine (3.143 g, 11.98 mmol), and phthalimide (882 mg, 5.99 mmol) were dissolved in 60 mL of THF. DIAD (2.33 mL, 11.98 mmol) was then added and the reaction mixture was stirred overnight at room temperature. The mixture was concentrated under vacuum, and the residue was chromatographed on silica gel using an ethyl acetate/heptane gradient. The title compound (1 g) was obtained as a clear oil.

Workup

  1. concentrationThe mixture was concentrated under vacuum
  2. customthe residue was chromatographed on silica gel using an ethyl acetate/heptane gradient

Sources & evidence

ORD record
ord-ca954aeb7cf542cd8f3810b5053b3583
Source dataset
uspto-grants-2013_03
Patent number
US08394858B2

Reaction notes

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