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

HRID 1053939Notes

Reaction equation

[OH:1][CH:2]1[CH:6]2[O:7][CH2:8][CH:9]([N:10]3[C:18](=[O:19])[C:17]4[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=4)[C:11]3=[O:20])[CH:5]2[O:4][CH2:3]1.C(N(CC)CC)C.[CH3:28][S:29](Cl)(=[O:31])=[O:30]>ClCCl.CN(C)C1C=CN=CC=1>[CH3:28][S:29]([O:1][CH:2]1[CH2:3][O:4][CH:5]2[CH:9]([N:10]3[C:18](=[O:19])[C:17]4[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=4)[C:11]3=[O:20])[CH2:8][O:7][CH:6]12)(=[O:31])=[O:30]

Participants

Conditions

Temperature: 0 °C

Procedure

Under a N2 atmosphere, to a solution of 2-(6-hydroxyhexahydrofuro[3,2-b]furan-3-yl)isoindoline-1,3-dione (2.35 g, 8.54 mmol) in dichloromethane (40 mL) were added triethylamine (1.30 g, 12.8 mmol) and N,N-dimethylpyridin-4-amine (209.2 mg, 1.7 mmol) and the mixture was cooled to 0° C. and then methanesulfonyl chloride (0.8 mL, 10.0 mmol) was added to the mixture. The resulting mixture was stirred at 0° C. for 30 min, then moved to room temperature overnight. The mixture was diluted with dichloromethane (100 mL), washed with 1M HCl (100 mL), water (100 mL) and brine (100 mL). The separated organic phase was dried over anhydrous Na2SO4, and then concentrated in vacuo. The residue was purified by silica gel column chromatography (MeOH/DCM (v/v)=1/200) to give the title compound as a white solid (2.35 g, 77.9%).

Workup

waitmoved to room temperature overnight
washwashed with 1M HCl (100 mL), water (100 mL) and brine (100 mL)
dry with materialThe separated organic phase was dried over anhydrous Na2SO4
concentrationconcentrated in vacuo
customThe residue was purified by silica gel column chromatography (MeOH/DCM (v/v)=1/200)

Sources & evidence

ORD record: ord-330e85e2380b47f296a8db814457b415
Source dataset: uspto-grants-2016_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09394281B2

Reaction notes

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