Ammonium Chloride → 1-tert-butyl 2-methyl (2S,4EZ)-4-(chloromethylene)-1,2-pyrrolidinedicarboxylate

Chloromethyltriphenylphosphonium iodide (270 mg, 0.62 mmol) was added to a solution of potassium tert-butoxide (67 mg, 0.59 mmol) in anhydrous diethyl ether (5 ml) under nitrogen and the resulting bright yellow mixture stirred for 30 minutes at ambient temperature. The reaction was then cooled to 0° C. and a solution of 1-tert-butyl 2-methyl (2S)-4-oxo-1,2-pyrrolidinedicarboxylate (100 mg, 0.41 mmol in 2 ml anhydrous diethyl ether) was added dropwise. The reaction was then warmed to room temperature and stirred for 30 minutes before adding saturated aqueous ammonium chloride solution (0.5 ml). The organic layer was removed in vacuo, and the aqueous washed with diethyl ether (3×5 ml). The combined organic layers were dried with brine and magnesium sulfate before filtering and removal of solvent. The desired product was isolated by silica gel chromatography, eluting with 15% ethyl acetate in hexanes to give 105 mg (93% yield) as a off-white wax.

1. temperatureThe reaction was then cooled to 0° C.
2. temperatureThe reaction was then warmed to room temperature
3. stirringstirred for 30 minutes
4. customThe organic layer was removed in vacuo
5. washthe aqueous washed with diethyl ether (3×5 ml)
6. dry with materialThe combined organic layers were dried with brine and magnesium sulfate
7. filtrationbefore filtering
8. customremoval of solvent

ORD-Eintrag

ord-0d963199445d45bcaaf30b3ad872da04

Quelldatensatz

uspto-grants-2006_03

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US07018988B2