Potassium Carbonate → Tert-butyl 1,3-dioxoisoindolin-2-yl(2-isopropoxyethyl)carbamate

HRID 220395

Reaction equation

CS(O[CH2:6][CH2:7][O:8][CH:9]([CH3:11])[CH3:10])(=O)=O.[O:12]=[C:13]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[C:15](=[O:22])[N:14]1[NH:23][C:24](=[O:30])[O:25][C:26]([CH3:29])([CH3:28])[CH3:27].C(=O)([O-])[O-].[K+].[K+]>C(#N)C.[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1.C(OCC)(=O)C.O>[O:22]=[C:15]1[C:16]2[C:21](=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:13](=[O:12])[N:14]1[N:23]([CH2:6][CH2:7][O:8][CH:9]([CH3:10])[CH3:11])[C:24](=[O:30])[O:25][C:26]([CH3:28])([CH3:27])[CH3:29]

Participants

Conditions

Temperature: 50 °C

Procedure

A round bottom flask charged with 2-isopropoxyethyl methanesulfonate (example 77A, 0.791 g, 4.34 mmol) in acetonitrile (21.70 mL) was stirred under an atmosphere of nitrogen. tert-Butyl 1,3-dioxoisoindolin-2-ylcarbamate (1.138 g, 4.34 mmol) was added along with potassium carbonate (2.399 g, 17.36 mmol) and benzyltriethylammonium chloride (0.198 g, 0.868 mmol). The reaction mixture was heated at 50° C. 24 h and cooled to rt over the weekend. The reaction mixture was diluted with ethyl acetate and water. The aqueous layer was extracted with ethyl acetate. The combined organics were washed with brine, dried over anhydrous sodium sulfate, vacuum filtered through a plug of silica gel and concentrated in vacuo. The crude oil was used without additional purification (1.26 g, 83% yield).

Workup

temperature24 h and cooled to rt over the weekend
extractionThe aqueous layer was extracted with ethyl acetate
washThe combined organics were washed with brine
dry with materialdried over anhydrous sodium sulfate, vacuum
filtrationfiltered through a plug of silica gel
concentrationconcentrated in vacuo
customThe crude oil was used without additional purification (1.26 g, 83% yield)

Sources & evidence

ORD record: ord-50c7568dcc72409cbf31471272f78f13
Source dataset: uspto-grants-2012_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08202881B2

Linked notes

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