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

HRID 128747

반응식

HRID 128747 반응식
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

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 962Water용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-8ec7e128fb84498fa001bb7b74ba420b
출처 데이터셋
uspto-grants-1995_11
특허 번호
US05464864

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