2-Butene, 1-bromo-3-methyl- → HCID 18922258, compound

A 2M solution of LDA (70.32 ml, 0.14 mol) was added (via syringe) to a solution of N-t-butoxycarbonyl-sarcosine methyl ester (26 g, 0.1279 mol) in 40 ml of dry THF at -78° C. under nitrogen and the mixture was stirred at this temperature for 30 minutes. To the above mixture was added 4-bromo-2-methyl-2-butene (20 g, 0.134 mol) with stirring continuing at -78° C., and the resulting mixture was allowed to warm to room temperature. The reaction mixture was quenched with 6 ml of saturated ammonium chloride solution at -78° C., 20 ml of water was added, and the resulting reaction mixture was extracted with ethyl acetate. The organic layer was washed with water and brine, dried over sodium sulfate, and concentrated in vacuo to yield a yellow oil, which was purified by silica gel column chromatography (20% ethyl acetate in hexane) to afford 22.1 g (63.7%) of N-t-butoxycarbonyl-2-(3-methyl-2-butenyl)-sarcosine methyl ester as an oil.

1. stirringwith stirring
2. customcontinuing at -78° C.
3. customThe reaction mixture was quenched with 6 ml of saturated ammonium chloride solution at -78° C.
4. addition20 ml of water was added
5. customthe resulting reaction mixture
6. extractionwas extracted with ethyl acetate
7. washThe organic layer was washed with water and brine
8. dry with materialdried over sodium sulfate
9. concentrationconcentrated in vacuo
10. customto yield a yellow oil, which
11. customwas purified by silica gel column chromatography (20% ethyl acetate in hexane)

ORD record

ord-15dc4105f0684585a24c9a5c775be723

Source dataset

uspto-grants-1996_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05512576