HCID 16307882, compound → HCID 20696594, compound

Methyl 1-(methylsulfonyl)pyrrolidine-2-carboxylate (1.1 g, 4.6 mmol) in anhydrous tetrahydrofuran (10 mL) was added slowly to a stirring suspension of lithium aluminum hydride (0.259 g, 6.8 mmol) in anhydrous tetrahydrofuran (10 mL) kept at 0° C. with an external ice bath. After fifteen minutes, the ice bath was removed and the reaction was allowed to warm to ambient temperature and stirred for an additional hour. The mixture was cooled to 0° C., and water (1 mL) was added dropwise, followed by 15% aqueous sodium hydroxide (1 mL), and water (3 mL). The mixture was stirred for 15 mins at room temperature, followed by the addition of magnesium sulfate and additional stirring. The mixture was filtered through Celite, washed three times with ether, and the combined organic fractions concentrated under reduced pressure to afford a yellow oil (0.7 g, 77%). 1H NMR (CDCl3, 300 MHz) δ 3.78-3.57 (m, 3H), 3.49-3.36 (m, 2H), 2.87 (s, 3H), 2.64 (br s, 1H), 2.09-1.82 (m, 4H).

1. customkept at 0° C. with an external ice bath
2. waitAfter fifteen minutes
3. customthe ice bath was removed
4. temperatureThe mixture was cooled to 0° C.
5. additionwater (1 mL) was added dropwise
6. stirringThe mixture was stirred for 15 mins at room temperature
7. additionfollowed by the addition of magnesium sulfate and additional stirring
8. filtrationThe mixture was filtered through Celite
9. washwashed three times with ether
10. concentrationthe combined organic fractions concentrated under reduced pressure

ORD record

ord-f207cd2dece048678c8c48ee76ce9353

Source dataset

uspto-grants-2016_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09265772B2