Iodoethane → Tert-butyl (1,3-dioxoisoindolin-2-yl)(ethyl)carbamate

HRID 1908025Notes

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[NH:12][C:13](=[O:19])[O:14][C:15]([CH3:18])([CH3:17])[CH3:16].I[CH2:21][CH3:22].C(=O)([O-])[O-].[K+].[K+]>[Br-].C([N+](CC)(CC)CC)C1C=CC=CC=1.C(#N)C.O>[O:11]=[C:4]1[C:5]2[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=2)[C:2](=[O:1])[N:3]1[N:12]([CH2:21][CH3:22])[C:13](=[O:19])[O:14][C:15]([CH3:16])([CH3:18])[CH3:17]

Participants

Conditions

Temperature: 50 °C

Procedure

tert-Butyl N-(1,3-dioxoisoindolin-2-yl)carbamate (1.0 g, 3.8 mmol), iodoethane (460 μL, 5.7 mmol), potassium carbonate (2.1 g, 15 mmol), and benzyl-triethyl-ammonium bromide (210 mg, 0.80 mmol) were combined in acetonitrile (15 mL) and heated at 50° C. for 48 h. The reaction mixture was diluted with water (30 mL) and was extracted with ether (3×15 mL). The combined organics were washed with brine, dried over sodium sulfate and evaporated to dryness. The crude material was purified by column chromatography (0-20% ethyl acetate in hexanes) to afford tert-butyl 1,3-dioxoisoindolin-2-yl(ethyl)-carbamate (0.79 g, 71%). ESI-MS m/z calc. 290.1. found 291.3 (M+1)+; Retention time: 1.64 minutes (3 min run). 1H NMR (400 MHz, CDCl3) δ 7.98-7.85 (m, 2H), 7.84-7.69 (m, 2H), 3.86-3.57 (m, 2H), 1.52 (s, 3H), 1.32 (s, 6H), 1.27-1.04 (m, 3H).

Workup

extractionwas extracted with ether (3×15 mL)
washThe combined organics were washed with brine
dry with materialdried over sodium sulfate
customevaporated to dryness
customThe crude material was purified by column chromatography (0-20% ethyl acetate in hexanes)

Sources & evidence

ORD record: ord-5a70391081e7493e9619ea537b5fc19c
Source dataset: uspto-grants-2013_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08598164B2

Reaction notes

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