Hydrochloric Acid → HCID 58865590, compound

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).

1. stirringthe solution was stirred for an additional 1 h
2. extractionextracted with CH2Cl2 (4×70 mL)
3. washThe organic phase was washed with saturated NaHCO3 (50 mL), brine (50 mL)
4. dry with materialdried over MgSO4
5. concentrationconcentrated
6. custompurified by column chromatography (0–5% MeOH in CH2Cl2)

ORD record

ord-cda7adb0c5ea4754806aae9f13131bed

Source dataset

uspto-grants-2007_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07223759B2