6-(1,3-Dioxoisoindolin-2-yl)hexahydrofuro[3,2-b]furan-3-yl methanesulfonate → 2-(6-Azidohexahydrofuro[3,2-b]furan-3-yl)isoindoline-1,3-dione

HRID 1053940Notes

Reaction equation

CS(O[CH:6]1[CH2:10][O:9][CH:8]2[CH:11]([N:14]3[C:22](=[O:23])[C:21]4[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=4)[C:15]3=[O:24])[CH2:12][O:13][CH:7]12)(=O)=O.[N:25]([Na])=[N+:26]=[N-:27]>CN(C=O)C.C(Cl)Cl>[N:25]([CH:6]1[CH:7]2[O:13][CH2:12][CH:11]([N:14]3[C:22](=[O:23])[C:21]4[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=4)[C:15]3=[O:24])[CH:8]2[O:9][CH2:10]1)=[N+:26]=[N-:27]

Participants

Conditions

Temperature: 140 °C

Procedure

To a solution of 6-(1,3-dioxoisoindolin-2-yl)hexahydrofuro[3,2-b]furan-3-yl methanesulfonate (2.80 g, 7.9 mmol) in DMF (60 mL) was added azido sodium (2.16 g, 33.2 mmol). The reaction was allowed to warm to 140° C. for 23 h. The solution was diluted with CH2Cl2 (100 mL), washed with water (100 mL×3) and dried over anhydrous Na2SO4, and then concentrated in vacuo to give the crude product. The product was used for next step without further purification.

Workup

washwashed with water (100 mL×3)
dry with materialdried over anhydrous Na2SO4
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-5863502c8e7d409989a0d9ef133e5367
Source dataset: uspto-grants-2016_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09394281B2

Reaction notes

Loading…