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

HRID 2218442

Reaction equation

[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

Participants

Conditions

Temperature: 0 °C

Procedure

(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)

Workup

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

Sources & evidence

ORD record: ord-18a0eca0641945b884f885252e04965b
Source dataset: uspto-grants-2008_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07411001B2

Linked notes

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