Ethanol → (2S,3R)-1-((2E,4Z)-(S)-1,2-Dimethyl-hexa-2,4-dienyl)-3-(3-oxo-propyl) pyrrolidine-2-carboxylic acid ethyl ester

Temperature

-70 °C

(2S,3R)-3-But-3-enyl-1-((S)-1-phenyl-ethyl)-pyrrolidine-2-carboxylic acid ethyl ester (1.0 g, 3.32 mmol) is dissolved in EtOH (10 mL) with HCl (0.5 mL, 37%), and cooled to −70° C. Ozone gas is bubbled though the solution for about 10 min or until the solution is turned very light blue color. The nitrogen gas is bubbled though the solution for 15 min to remove excess ozone in the solution. To the cool solution is added Zn dust (0.43 g. 6.6 mmol) and HCl (0.5 mL, 37%), and stirred at r.t. for 20 min. After filtration the solution is diluted with 50 mL of CH2Cl2 and washed with saturated NaHCO3 (10 mL) and 2×20 ml of water. After dried and concentrated, a colorless liquid (1.0 g) is obtained without further purification for next step reaction. (NMR and MS data confirmed, U-4117-51-30).

1. customOzone gas is bubbled though the solution for about 10 min or until the solution
2. customThe nitrogen gas is bubbled though the solution for 15 min
3. customto remove excess ozone in the solution
4. filtrationAfter filtration the solution
5. additionis diluted with 50 mL of CH2Cl2
6. washwashed with saturated NaHCO3 (10 mL) and 2×20 ml of water
7. customAfter dried
8. concentrationconcentrated

ORD record

ord-8e8dd83115f64f3dae85f909901f32f5

Source dataset

uspto-grants-2012_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08207183B2