1-Iodo-2-methoxyethane → Methyl(1S,4S)-4-[(tert-Butoxycarbonyl)amino]-1-(2-methoxyethyl)cyclopent-2-ene-1-carboxylate

온도

-78 °C

To a 1.00 M solution of lithium hexamethyldisilazide in tetrahydrofuran (9.1 mL, 9.1 mmmol) under N2 at −78° C. was added a solution of methyl (1R,4S)-4-[(tert-butoxycarbonyl)amino]cyclopent-2-ene-1-carboxylate (1.0 g, 4.1 mmol) in tetrahydrofuran (2.0 mL). The resulted light brown solution was stirred at −78° C. for 30 min before adding a solution of 1-iodo-2-methoxyethane (0.93 g, 5.0 mmol) in tetrahydrofuran (2.0 mL). The mixture was stirred for an hour at −78° C. then kept in a freezer reading at −20° C. overnight. The reaction was quenched with saturated ammonium chloride. The layers were separated and the aqueous extracted with ether three times. The combined organics were then washed with brine, dried (magnesium sulfate), filtered and purified by flash chromatography (EtOAc/Hexane) to provide the desired product (0.28 g, 23%). LCMS calculated for C15H26NO5: (M+H) 300.2; found 300.2.

1. stirringThe mixture was stirred for an hour at −78° C.
2. waitthen kept in a freezer reading at −20° C. overnight
3. customThe reaction was quenched with saturated ammonium chloride
4. customThe layers were separated
5. extractionthe aqueous extracted with ether three times
6. washThe combined organics were then washed with brine
7. dry with materialdried (magnesium sulfate)
8. filtrationfiltered
9. custompurified by flash chromatography (EtOAc/Hexane)

ORD 기록

ord-60d4d87c1df4495cab843cd4e6456894

출처 데이터셋

uspto-grants-2008_11

DOI

10.6084/m9.figshare.5104873.v1

특허 번호

US07449467B2