N-Hydroxyphthalimide → 2-(1-Hydroxymethyl-cyclopropylmethoxy)-isoindole-1,3-dione

HRID 2218442

반응식

HRID 2218442 반응식
[OH:1][CH2:2][C:3]1([CH2:6][OH:7])[CH2:5][CH2:4]1.O[N:9]1[C:13](=[O:14])[C:12]2=[CH:15][CH:16]=[CH:17][CH:18]=[C:11]2[C:10]1=[O:19].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>O1CCCC1>[OH:1][CH2:2][C:3]1([CH2:6][O:7][N:9]2[C:13](=[O:14])[C:12]3[C:11](=[CH:18][CH:17]=[CH:16][CH:15]=3)[C:10]2=[O:19])[CH2:5][CH2:4]1

참가 물질

6

반응물 4

HCID 10665N-HydroxyphthalimideHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 41014371,1-Bis(hydroxymethyl)cyclopropane

생성물 1

HCID 692205082-(1-Hydroxymethyl-cyclopropylmethoxy)-isoindole-1,3-dione수율 57%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

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온도
0 °C

실험 절차

(1-Hydroxymethyl-cyclopropyl)-methanol (4.08 g, 0.04 mol), N-hydroxyphthalimide (6.53 g, 0.04 mol) and triphenylphosphine (10.50 g, 0.04 mol) were combined in anhydrous tetrahydrofuran (100 mL) and stirred at 0° C. for 1.5 hours. Diethyl azodicarboxylate (6.97 g, 0.04 mol) was added at 0° C. and the reaction mixture was stirred at room temperature overnight. Repeated concentration of the reaction mixture from chloroform and filtration of the resulting precipitate (triphenylphosphine oxide) afforded the crude product which was further purified by silica gel chromatography. Elution with hexane/ethyl acetate (3:2) provided 2-(1-Hydroxymethyl-cyclopropylmethoxy)-isoindole-1,3-dione (5.63 g, 57% yield) as a white solid: 1H NMR (400 MHz; CDCl3) δ 7.82-7.85 (2H, m), 7.74-7.78 (2H, m), 4.19 (2H, s), 3.72 (2H, s), 0.63 (4H, s)

후처리

  1. stirringthe reaction mixture was stirred at room temperature overnight
  2. filtrationfrom chloroform and filtration of the resulting precipitate (triphenylphosphine oxide)
  3. customafforded the crude product which
  4. customwas further purified by silica gel chromatography
  5. washElution with hexane/ethyl acetate (3:2)

출처 및 근거

ORD 기록
ord-18a0eca0641945b884f885252e04965b
출처 데이터셋
uspto-grants-2008_08
특허 번호
US07411001B2

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