반응 #1348873

반응 방정식

lithium hexamethyldisilazide

methyl (1R,4S)-4-[(tert-butoxycarbonyl)amino]cyclopent-2-ene-1-carboxylate

1-iodo-2-methoxyethane

→

desired product

수율 23.0%

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

수율 23.0%

용매

tetrahydrofuran

tetrahydrofuran

tetrahydrofuran

반응 조건

후처리

1. 1
   workup.STIRRINGThe mixture was stirred for an hour at −78° C.
2. 2
   workup.WAITthen kept in a freezer reading at −20° C. overnight
3. 3
   기타The reaction was quenched with saturated ammonium chloride
4. 4
   기타The layers were separated
5. 5
   추출the aqueous extracted with ether three times
6. 6
   세척The combined organics were then washed with brine
7. 7
   건조dried (magnesium sulfate)
8. 8
   여과filtered
9. 9
   기타purified by flash chromatography (EtOAc/Hexane)

실험 절차

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.

출처