Tetrahydrofuran → HCID 86652147, compound

HRID 1258131Notes

Reaction equation

Cl[C:2]1[CH2:6][CH2:5][C:4](=[O:7])[CH:3]=1.N1[CH2:10][CH2:9]1.C([N:13]([CH2:16][CH3:17])[CH2:14]C)C.[O:18]1[CH2:22][CH2:21][CH2:20][CH2:19]1>>[CH3:22][O:18][C:19]1[CH:20]=[CH:21][C:17]([CH:16]2[CH2:14][N:13]2[C:2]2[CH2:6][CH2:5][C:4](=[O:7])[CH:3]=2)=[CH:10][CH:9]=1

Participants

Reactant 4

HCID 8028Tetrahydrofuran2×

HCID 8471Triethylamine

HCID 9033Aziridine

HCID 406162-Cyclopenten-1-one, 3-chloro-

Product 1

HCID 86652147HCID 86652147, compoundYield 16%

Conditions

Temperature: 25 °C

Procedure

A solution of chloroenone 16 (16 mg, 0.14 mmol, 1.0 equiv) in tetrahydrofuran (1.0 mL) at 25° C. was transferred via cannula to a stirred solution of aziridine 14 (25 mg, 0.17 mmol, 1.2 equiv) and triethylamine (35 μL, 0.25 mmol, 1.5 equiv) in tetrahydrofuran (1.0 mL) at 25° C. The resulting brown solution was stirred at 25° C. for 24 h. The reaction mixture was concentrated by rotary evaporation. The residue was purified by silica gel column chromatography (5% triethylamine and 20% ethyl acetate in benzene) to afford 18 (5 mg, 16% yield) as a yellow film. Rf=0.29 (5% triethylamine and 20% ethyl acetate in benzene); 1H NMR (500 MHz, C6D6) δ 7.00 (m, 2H, ArH), 6.76 (m, 2H, ArH), 5.43 (t, 1H, J=1.5 Hz, vinyl H), 3.28 (s, 3H, OCH3), 2.45 (dd, 1H, J=6, 3 Hz, ArCHN), 2.11 (m, 2H, CH2), 1.85-2.00 (m, 2H, CH2), 1.77 (dd, 1H, J=3, 1 Hz, CH2N), 1.63 (dd, 1H, J=6, 1 Hz, CH2N).

Workup

customat 25° C.
concentrationThe reaction mixture was concentrated by rotary evaporation
customThe residue was purified by silica gel column chromatography (5% triethylamine and 20% ethyl acetate in benzene)

Sources & evidence

ORD record: ord-b9dc01b0f56f462487fe127e3b502aec
Source dataset: uspto-grants-2013_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08466142B2

Reaction notes

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