Ammonia → (R)-2-amino-3-(3,4-diethyl-phenyl)-N-((1S,2S)-2-hydroxy-1-methyl-2-phenyl-ethyl)-N-methyl-propionamide

Temperature

0 °C

In a three-necked flask 250 mL of a 1 molar solution of lithium-bis-(trimethylsilyl)-amide (250 mmol) and 15.4 g (64.1 mmol) of (1S,2S)-pseudoephedrine-glycinamide hydrate were added to 500 mL of THF under a nitrogen atmosphere and while cooling with ice. The mixture was stirred for 1.5 h at 0° C., slowly combined with 15.4 g (67.1 mmol) of 4-bromomethyl-1,2-diethyl-benzene, dissolved in 10 mL of THF, and stirred for 2 h at 0° C. While cooling with ice 10 mL of water and 6 mL semiconcentrated HCl were added dropwise, stirred for a further 20 min and made alkaline with concentrated ammonia solution. The reaction mixture was exhaustively extracted with EtOAc, the combined organic phases were dried and evaporated down under reduced pressure. The residue remaining was purified through silica gel. The desired product was obtained in the form of a solid.

1. temperaturewhile cooling with ice
2. stirringstirred for 2 h at 0° C
3. additionwere added dropwise
4. stirringstirred for a further 20 min
5. extractionThe reaction mixture was exhaustively extracted with EtOAc
6. customthe combined organic phases were dried
7. customevaporated down under reduced pressure
8. customThe residue remaining was purified through silica gel

ORD record

ord-03f27a86128147e1b795a455199b04b8

Source dataset

uspto-grants-2010_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07700589B2