Pyrrolidine → 2-[3-(pyrrolidin-1-ylsulfonyl)propyl]-1H-isoindole-1,3(2H)-dione

HRID 1371391Notes

Reaction equation

[O:1]=[C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4](=[O:11])[N:3]1[CH2:12][CH2:13][CH2:14][S:15](Cl)(=[O:17])=[O:16].C([N:22]([CH2:26][CH3:27])[CH:23]([CH3:25])C)(C)C.N1CCCC1>O1CCCC1>[N:22]1([S:15]([CH2:14][CH2:13][CH2:12][N:3]2[C:2](=[O:1])[C:10]3[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=3)[C:4]2=[O:11])(=[O:17])=[O:16])[CH2:23][CH2:25][CH2:27][CH2:26]1

Participants

Conditions

Temperature: 22 °C

Procedure

A solution of 3-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)propane-1-sulfonyl chloride (0.288 g) in dry tetrahydrofuran (5 ml) was treated with N,N-diisopropylethylamine (0.350 ml) and pyrrolidine (0.10 ml) at 22° C. under nitrogen, and the mixture was stirred at 22° C. for 1 h. After standing overnight at room temperature, the mixture was partitioned between saturated aqueous sodium bicarbonate (10 ml) and ethyl acetate (2×10 ml). The organic layers were washed with brine, dried (MgSO4) and evaporated in vacuo to give a white solid (0.145 g).

Workup

waitAfter standing overnight at room temperature
customthe mixture was partitioned between saturated aqueous sodium bicarbonate (10 ml) and ethyl acetate (2×10 ml)
washThe organic layers were washed with brine
dry with materialdried (MgSO4)
customevaporated in vacuo

Sources & evidence

ORD record: ord-ba8c723901e04e50846e4c072c9b295c
Source dataset: uspto-grants-2007_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07157457B2

Reaction notes

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