Ammonium Chloride → (S)-3-[Benzyl-((S)-1-phenyl-ethyl)-amino]-hexanoic acid ethyl ester

온도

-78 °C

To a solution of (S)-(−)-N-benzyl-alpha-methyl-benzylamine (50 mL, 239 mmol) in THF (150 mL) at 0° C. is added nBuLi (2.5 M in THF) (100 mL, 250 mmol) under nitrogen atmosphere. The solution is cooled to −78° C. and ethyl trans-2-hexenoate (16.6 g, 117 mmol) is added. The solution is stirred for 1 hour and saturated NH4Cl solution is added. The solution is warmed to room temperature and is extracted with EtOAc. The combined organic layer is dried with MgSO4 and is filtered. The filtrate is concentrated and the residue is purified by flash chromatography with 5% EtOAc in Hexane as the eluent to afford the (S)-3-[Benzyl-((S)-1-phenyl-ethyl)-amino]-hexanoic acid ethyl ester (20.8 g, 50%) as a colorless oil.

1. temperatureThe solution is warmed to room temperature
2. extractionis extracted with EtOAc
3. dry with materialThe combined organic layer is dried with MgSO4
4. filtrationis filtered
5. concentrationThe filtrate is concentrated
6. customthe residue is purified by flash chromatography with 5% EtOAc in Hexane as the eluent

ORD 기록

ord-46acb57131954e39b0b4a0339f750930

출처 데이터셋

uspto-grants-2013_02

DOI

10.6084/m9.figshare.5104873.v1

특허 번호

US08377949B2