Tetrahydrofuran → trans-2-(4-Hydroxycyclohexyl)-isoindole-1,3-dione

HRID 1683251Notes

Reaction equation

HRID 1683251 reaction equation
Cl.[NH2:2][CH:3]1[CH2:8][CH2:7][CH:6]([OH:9])[CH2:5][CH2:4]1.C(=O)(O)[O-].[Na+].C(N1[C:24](=[O:25])[C:23]2=[CH:26][CH:27]=[CH:28][CH:29]=[C:22]2[C:21]1=[O:30])(OCC)=O.O1CCCC1>O>[C:21]1(=[O:30])[N:2]([CH:3]2[CH2:8][CH2:7][CH:6]([OH:9])[CH2:5][CH2:4]2)[C:24](=[O:25])[C:23]2=[CH:26][CH:27]=[CH:28][CH:29]=[C:22]12

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 31187N-CarbethoxyphthalimideHCID 516892Sodium BicarbonateHCID 522619(1s,4s)-4-Aminocyclohexan-1-ol hydrochloride

Product 1

HCID 288726trans-2-(4-Hydroxycyclohexyl)-isoindole-1,3-dioneYield 72.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 4-aminocyclohexanol hydrochloride (6.08 g, 0.04 mole) in water (60 ml) was brought to pH 8 with aqueous sodium bicarbonate solution. N-carbethoxy-phthalimide (8.76 g, 0.04 mole) was added followed by tetrahydrofuran (until homogenous solution was obtained). The clear solution was stirred at room temperature overnight. During this time a white solid was precipitated. The tetrahydrofuran was removed in vacuo and the remaining aqueous solution was extracted with ethyl acetate until the solution was clear. The ethyl acetate extracts were combined, washed with water, dried (MgSO4) and concentrated to give 4-phthalimido cyclohexanol as a white solid (7.1 g).

Workup

  1. customDuring this time a white solid was precipitated
  2. customThe tetrahydrofuran was removed in vacuo
  3. extractionthe remaining aqueous solution was extracted with ethyl acetate until the solution
  4. washwashed with water
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-bc3e9e8082a245308ac1288598f482cb
Source dataset
uspto-grants-1997_06
Patent number
US05637611

Reaction notes

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