1-(2,5-dihydropyrrol-1-yl)-2,2,2-trifluoroethanone

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Compound 320 (22.0 mmol) and N-methylmorpholine N-oxide monohydrate (35.0 mmol) were dissolved in a mixture of acetone and H2O (1:1, v/v; 60 mL). OsO4 (0.4 mmol, 2 mol %) was added and the resulting pale yellow solution was stirred at room temperature for 16 h. Na2S2O5 (3.9 mmol) was then added and the solution was stirred for an additional 1 h. The solution was acidified to pH=2 with 6 M HCl and extracted with CH2Cl2 (4×70 mL). The organic phase was washed with saturated NaHCO3 (50 mL), brine (50 mL), dried over MgSO4, concentrated and purified by column chromatography (0–5% MeOH in CH2Cl2) to give 1-(cis-3,4-Dihydroxy-pyrrolidin-1-yl)-2,2,2-trifluoro-ethanone (321) (17 mmol, 78% yield) as a colorless oil. 1H NMR (400 MHz, CD3OD) δ=3.95 ppm (dd, 1H, J=4, 13 Hz), 3.59 (dd, 1 H, J=6, 12 Hz), 3.65 (dd, 1H, J=6, 13 Hz), 3.84 (dd, 1H, J=5, 12 Hz), 4.19–4.27 (m, 2H). the solution was stirred for an additional 1 h extracted with CH2Cl2 (4×70 mL) The organic phase was washed with saturated NaHCO3 (50 mL), brine (50 mL) dried over MgSO4 concentrated purified by column chromatography (0–5% MeOH in CH2Cl2)

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a stirred solution of 319 (26.9 mmol) in freshly distilled CH2Cl2 (250 mL), under nitrogen (1 atm) was added Grubb's Catalyst {RuCl2(CHC6H5)[P(C6H11)2], 0.5 mol %}. After 1.5 h stirring at room temperature, TLC indicated complete conversion of the starting material to a more polar product. The reaction was quenched by bubbling air through the solution. The solution was concentrated and subjected to chromatography purification (5–20% EtOAc in hexanes) to yield 1-(2,5-dihydro-pyrrol-1-yl)-2,2,2-trifluoro-ethanone (320) (22.0 mmol, 82% yield). The reaction was quenched by bubbling air through the solution The solution was concentrated subjected to chromatography purification (5–20% EtOAc in hexanes)

Conditions: temp:0.00; pressure:0.00; stir: