Phthalimide → HCID 53955981, compound

HRID 274084Notes

Reaction equation

HRID 274084 reaction equation
[CH3:1][O:2][C:3]1[CH:14]=[CH:13][C:6]2[CH2:7][CH2:8][CH2:9][C@H:10](O)[CH2:11][C:5]=2[CH:4]=1.[C:15]1(=[O:25])[NH:19][C:18](=[O:20])[C:17]2=[CH:21][CH:22]=[CH:23][CH:24]=[C:16]12.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>O1CCCC1>[CH3:1][O:2][C:3]1[CH:14]=[CH:13][C:6]2[CH2:7][CH2:8][CH2:9][C@@H:10]([N:19]3[C:18](=[O:20])[C:17]4=[CH:21][CH:22]=[CH:23][CH:24]=[C:16]4[C:15]3=[O:25])[CH2:11][C:5]=2[CH:4]=1

Participants

6

Reactant 4

HCID 6809PhthalimideHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 53929887HCID 53929887, compound

Product 1

HCID 53955981HCID 53955981, compoundYield 25.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a mixture of (S)-3-methoxy-6,7,8,9-tetrahydro-5H-benzocyclohepten-6-ol (1.00 g), phthalimide (0.77 g), and triphenylphosphine (1.36 g) in dry tetrahydrofuran, was added dropwise a solution of diethyl azodicarboxylate (0.91 g) in dry tetrahydrofuran (3 ml) at 26° C.~33° C. The mixture was stirred at ambient temperature for 2 days. The solvent was evaporated in vacuo. Diethyl ether (30 ml) was added to the residue and the mixture was stirred and the resulting precipitates (triphenyl phosphinoxide) were removed by filtration. The filtrate was evaporated in vacuo. The residue was purified by column chromatography (silica gel, n-hexane:ethyl acetate=5:1) to give (R)-N-(3-methoxy-6,7,8,9-tetrahydro-5H-benzocyclohepten-6-yl)phthalimide as a white powder (0.43 g).

Workup

  1. customThe solvent was evaporated in vacuo
  2. additionDiethyl ether (30 ml) was added to the residue
  3. stirringthe mixture was stirred
  4. customthe resulting precipitates (triphenyl phosphinoxide)
  5. customwere removed by filtration
  6. customThe filtrate was evaporated in vacuo
  7. customThe residue was purified by column chromatography (silica gel, n-hexane:ethyl acetate=5:1)

Sources & evidence

ORD record
ord-9e26ad224ae246c18d78eacf9e69e79c
Source dataset
uspto-grants-1995_02
Patent number
US05387710

Reaction notes

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