[C:1]([CH2:3]P(=O)(OCC)OCC)#[N:2].CC(C)([O-])C.[K+].[N:18]12[CH2:25][CH:22]([CH2:23][CH2:24]1)[CH2:21][C:20](=O)[CH2:19]2.C(=O)([O-])[O-].[K+].[K+]>C1COCC1>[C:1]([CH:3]=[C:20]1[CH2:21][CH:22]2[CH2:25][N:18]([CH2:24][CH2:23]2)[CH2:19]1)#[N:2]Diethyl cyanomethylphosphonate (5.67 g, 0.032 mole) in THF (75 ml) was added over 10 minutes to a stirred solution of potassium tert-butoxide (3.60 g, 0.032 mole) in THF (75 ml) at 0° C. The reaction mixture was then cooled to -20° C. before dropwise addition of 1-azabicyclo[3.2.11octan-3-one* (3.64 g, 0.029 mole) in THF (50 ml) over 15 minutes. The mixture was allowed to warm to room temperature, stirred for 1h, and then poured into 20% aqueous potassium carbonate (150 ml) and extracted with ethyl acetate (3×200 ml). The combined organic extracts were dried (Na2SO4) and evaporated to give the title compound (D11) as a 6:5 mixture of E and Z isomers (3.88 g, 90%). The isomers could be separated chromatographically on silica using 3% methanol/chloroform as eluant to give in order of elution the Z-isomer and the E-isomer as oils.
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