Triethylamine → HCID 73234970, compound

HRID 1258135Notes

Reaction equation

C(N(CC)CC)C.Cl[C:9]1[CH:13]2[O:14][C:15]([CH3:18])([CH3:17])[O:16][CH:12]2[C:11](=[O:19])[CH:10]=1.[O:20]1[C:24]2[CH:25]=[CH:26][C:27]([CH:29]3[CH2:31][NH:30]3)=[CH:28][C:23]=2[O:22][CH2:21]1>O1CCCC1>[O:20]1[C:24]2[CH:25]=[CH:26][C:27]([CH:29]3[CH2:31][N:30]3[C:9]3[CH:13]4[O:14][C:15]([CH3:18])([CH3:17])[O:16][CH:12]4[C:11](=[O:19])[CH:10]=3)=[CH:28][C:23]=2[O:22][CH2:21]1

Participants

Conditions

Temperature: 25 °C

Procedure

Triethylamine (0.4 mL, 3.0 mmol, 2.0 equiv) and β-chloroenone 53 (280 mg, 1.5 mmol, 1.0 equiv) were sequentially added to a stirred solution of aziridine 15 (360 mg, 2.2 mmol, 1.5 equiv) in tetrahydrofuran (10 mL) at 25° C. The resulting white mixture was stirred at 25° C. for 3 h. The crude reaction mixture was loaded directly onto a column and purified by silica gel column chromatography (1% triethylamine and 49% benzene in ethyl acetate) to afford 54 (400 mg, 85% yield) as a yellow foam. Rf=0.68 (1% triethylamine and 49% benzene in ethyl acetate); 1H NMR (500 MHz, C6D6) δ 6.55-6.70 (m, 3H, ArH), 5.24-5.28 (m, 2H, OCH2O), 5.14-5.18 (m, 1H, NCCH), 4.50-4.56 (m, 1H, CH(OR)), 4.19-4.27 (m, 1H, CH(OR)), 2.46-3.18 (m, 1H, ArCHN), 1.84-2.17 (m, 1H, CH2N), 1.63-1.78 (m, 1H, CH2N), 1.28-1.32 (m, 3H, CH3), 1.10-1.12 (m, 3H, CH3); IR (neat film) 2989 (w), 1703 (m), 1586 (s) cm−1; HRMS (ESI) m/z: Calcd for C17H18NO5 (MO 316.1185; observed 316.1186.

Workup

customThe crude reaction mixture
custompurified by silica gel column chromatography (1% triethylamine and 49% benzene in ethyl acetate)

Sources & evidence

ORD record: ord-e1d130addbca4ee2a41aa1ef437cf719
Source dataset: uspto-grants-2013_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08466142B2

Reaction notes

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