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

Temperatur

-78 °C

To a 1.00 M solution of lithium hexamethyldisilazide in tetrahydrofuran (9.1 mL, 9.1 mmol) 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-Eintrag

ord-b28bf8574a494abc991b652dee8c9fdd

Quelldatensatz

uspto-grants-2013_06

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08470827B2