Phthalimide → HCID 19047345, compound

HRID 1780765Notes

Reaction equation

HRID 1780765 reaction equation
[C:1]1(=[O:11])[NH:5][C:4](=[O:6])[C:3]2=[CH:7][CH:8]=[CH:9][CH:10]=[C:2]12.[O:12]1[CH:18]2[CH:13]1[CH:14]=[CH:15][CH2:16][CH2:17]2>[Pd].O1CCCC1>[OH:12][CH:13]1[CH2:18][CH2:17][CH:16]=[CH:15][CH:14]1[N:5]1[C:1](=[O:11])[C:2]2=[CH:10][CH:9]=[CH:8][CH:7]=[C:3]2[C:4]1=[O:6]

Participants

5

Reactant 2

HCID 6809PhthalimideHCID 1608667-Oxabicyclo[4.1.0]hept-2-ene

Product 1

HCID 19047345HCID 19047345, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

If 19.11 g (0.13 mol) of phthalimide are reacted with 0.6 mol % of the palladium(0) catalyst prepared in situ as described above and one equivalent of 3,4-epoxycyclohexene in tetrahydrofuran first at 0° C. and then for 4 hours at the reflux temperature, 1.45 g (4.6% of theory) of [(1RS,2SR)-2-hydroxy-1-phthalimido-cyclohex-5-ene of melting point 112° to 114° C. are obtained after purification by chromatography over silica gel using ethyl acetate/cyclohexane 3/2. 1H NMR (270 MHz, d6 -DMSO); δ[ppm]: 7.83 (m, 4H), 5.90 (m, 1H), 5.63 (m, 1H), 4.84 (d, 1H), 4.75 (m, 1H), 3.90 (m, 1H), 2.27 (m, 1H), 2.1-1.65 (m, 3H).

Workup

  1. customprepared in situ
  2. customfirst at 0° C.

Sources & evidence

ORD record
ord-f41944dbd74a452ebef29c79fa256e46
Source dataset
uspto-grants-1997_05
Patent number
US05631259

Reaction notes

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