Phthalimide → N-[(1,2,3,4-tetrahydro-5-methoxy-2-naphthyl)methyl]phthalimide

HRID 344042Notes

Reaction equation

HRID 344042 reaction equation
N(C(OCC)=O)=NC(OCC)=O.[CH3:13][O:14][C:15]1[CH:24]=[CH:23][CH:22]=[C:21]2[C:16]=1[CH2:17][CH2:18][CH:19]([CH2:25]O)[CH2:20]2.[C:27]1(=[O:37])[NH:31][C:30](=[O:32])[C:29]2=[CH:33][CH:34]=[CH:35][CH:36]=[C:28]12.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>O1CCCC1>[CH3:13][O:14][C:15]1[CH:24]=[CH:23][CH:22]=[C:21]2[C:16]=1[CH2:17][CH2:18][CH:19]([CH2:25][N:31]1[C:30](=[O:32])[C:29]3=[CH:33][CH:34]=[CH:35][CH:36]=[C:28]3[C:27]1=[O:37])[CH2:20]2

Participants

6

Reactant 4

HCID 6809PhthalimideHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 53744579(5-Methoxy-1,2,3,4-tetrahydronaphthalen-2-yl)methanol

Product 1

HCID 70187305N-[(1,2,3,4-tetrahydro-5-methoxy-2-naphthyl)methyl]phthalimideYield 55.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of diethyl azodicarboxylate (871 mg) in tetrahydrofuran (4 ml) was added slowly to a stirred solution of (1,2,3,4-tetrahydro-5-methoxy-2-naphthyl)methanol (961 mg), phthalimide (736 mg), and triphenylphosphine (1.31 g) in tetrahydrofuran (10 ml) at room temperature and the resulting mixture was stirred at the same temperature for 24 hours. The reactIon mixture was evaporated in vacuo and the residue was chromatographed (toluene) over silica gel. The eluate was evaporated in vacuo and the residue was triturated with n-hexane to afford N-[(1,2,3,4-tetrahydro-5-methoxy-2-naphthyl)methyl]phthalimide (888 mg) as a colorless powder.

Workup

  1. customThe reactIon mixture was evaporated in vacuo
  2. customthe residue was chromatographed (toluene) over silica gel
  3. customThe eluate was evaporated in vacuo
  4. customthe residue was triturated with n-hexane

Sources & evidence

ORD record
ord-429afd942f904fd09421bf673be5bc7c
Source dataset
uspto-grants-1999_01
Patent number
US05863918

Reaction notes

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