Hydrogen Peroxide → HCID 68887618, compound

Temperature

50 °C

A solution of 8-cyano-6-phenyl-3,4-dihydro-1H-pyrrolo[1,2-a]pyrazine-2-carboxylic acid tert-butyl ester (3.87 g, Reference Example 4(a)) in methanol (200 mL) was treated with a 10M aqueous solution of sodium hydroxide (10.45 mL), then with a 27.5% w/w aqueous solution of hydrogen peroxide (0.74 mL). After stirring at 50° C. for 0.75 hour the reaction mixture was further treated with a 27.5% w/w aqueous solution of hydrogen peroxide (0.74 mL). After further stirring at 50° C. for 2 hours the reaction mixture was then further treated with a 27.5% w/w aqueous solution of hydrogen peroxide (0.74 mL). After further stirring at 50° C. for 1.5 hours the reaction mixture was allowed to cool to room temperature and treated with a saturated aqueous solution of sodium thiosulfate (20 mL). After stirring at room temperature for 15 minutes the reaction mixture was evaporated and then treated with ethyl acetate (650 mL) and water (150 mL). The organic phase was separated, washed with water (150 mL) and then dried over sodium sulfate. The organic phase was then evaporated to give the title compound (4.06 g) as a white solid, m.p. 208–210° C. MS: 342 [MH]+.

1. stirringAfter further stirring at 50° C. for 2 hours the reaction mixture
2. stirringAfter further stirring at 50° C. for 1.5 hours the reaction mixture
3. temperatureto cool to room temperature
4. stirringAfter stirring at room temperature for 15 minutes the reaction mixture
5. customwas evaporated
6. additiontreated with ethyl acetate (650 mL) and water (150 mL)
7. customThe organic phase was separated
8. washwashed with water (150 mL)
9. dry with materialdried over sodium sulfate
10. customThe organic phase was then evaporated

ORD record

ord-9092977c1c724eddae19117d14549001

Source dataset

uspto-grants-2006_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07148215B2