Tetrahydrofuran → HCID 58195999, compound

HRID 1258130Notes

Reaction equation

HRID 1258130 reaction equation
Cl[C:2]1[CH2:6][CH2:5][C:4](=[O:7])[CH:3]=1.[NH:8]1[CH2:10][CH2:9]1.C(N([CH2:16][CH3:17])CC)C.O1[CH2:22][CH2:21][CH2:20][CH2:19]1>>[C:17]1([CH:9]2[CH2:10][N:8]2[C:2]2[CH2:6][CH2:5][C:4](=[O:7])[CH:3]=2)[CH:16]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

5

Reactant 4

HCID 8028Tetrahydrofuran2×HCID 8471TriethylamineHCID 9033AziridineHCID 406162-Cyclopenten-1-one, 3-chloro-

Product 1

HCID 58195999HCID 58195999, compoundYield 58%

Conditions

Temperature
60 °C

Procedure

A solution of chloroenone 16 (140 mg, 1.2 mmol, 1.1 equiv) in tetrahydrofuran (3.5 mL) at 25° C. was transferred via cannula to a stirred solution of aziridine 13 (130 mg, 1.1 mmol, 1.0 equiv) and triethylamine (0.19 mL, 1.4 mmol, 1.2 equiv) in tetrahydrofuran (4.0 mL) at 25° C. The reaction vessel was sealed under argon and heated to 60° C. via oil bath for 24 h. The reaction mixture was cooled to 25° C. and concentrated by rotary evaporation. The residue was purified by silica gel column chromatography (5% triethylamine in ethyl acetate) to afford 17 (130 mg, 58% yield) as a brown oil. Rf=0.56 (5% triethylamine in ethyl acetate); 1H NMR (500 MHz, C6D6) δ 7.05-7.15 (m, 5H, ArH), 5.39 (t, 1H, J=1.5 Hz, vinyl H), 2.41 (dd, 1H, J=6, 3 Hz, ArCHN), 2.08 (m, 2H, CH2), 1.85-1.95 (m, 2H, CH2), 1.73 (dd, 1H, J=3, 1 Hz, CH2N), 1.60 (dd, 1H, J=6, 1 Hz, CH2N).

Workup

  1. customat 25° C.
  2. customThe reaction vessel was sealed under argon
  3. temperatureThe reaction mixture was cooled to 25° C.
  4. concentrationconcentrated by rotary evaporation
  5. customThe residue was purified by silica gel column chromatography (5% triethylamine in ethyl acetate)

Sources & evidence

ORD record
ord-7c009e9b263d4a3fa1edb52afd1ebc04
Source dataset
uspto-grants-2013_06
Patent number
US08466142B2

Reaction notes

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