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ChemicalBook CAS DataBase List (2S,3R)-1-(Dimethylamino)-3-(3-methoxyphenyl)-2-methylpentan-3-ol

(2S,3R)-1-(Dimethylamino)-3-(3-methoxyphenyl)-2-methylpentan-3-ol synthesis

3synthesis methods
-

Yield:809282-20-0 99%

Reaction Conditions:

Stage #1: (2S)-3-dimethylamino-1-(3-methoxyphenyl)-2-methyl-1-propanone;ethylmagnesium bromide in tetrahydrofuran at 15; for 4 h;Grignard Reaction;
Stage #2: with ammonium bisulphate;water in tetrahydrofuran at 5;Product distribution / selectivity;

Steps:

a.2

2. (S)-3-(Dimethylamino)-1-(3-methoxyphenyl)-2-methylpropan-1-one (774.6 g, 3.5 mol, ee 95 %) was dissolved in dry tetrahydrofuran (800 mL) in a 10 L double jacket vessel equipped with an electrical impeller stirrer, a gas transition line, PtIOO temperature measuring equipment and an oil based cooling/heating system and ethyl magnesium bromide (2 L, 2 M in THF) was added at a temperature of 15 °C within 2 hours. The reaction mixture was stirred for two hours at that temperature, cooled to 5 0C and aqueous ammonium hydrogen sulfate solution (10 % by weight, 2L) was added. The phases were separated and the organic phase was concentrated in vacuo at 40 0C until a pressure of 5 mbar was reached. (2S,3R)-1-(Dimethylamino)- 3-(3-methoxyphenyl)-2-methylpentan-3-ol (871.1 g, 99 %) was obtained as a colorless oil (ee 95 %).

References:

WO2008/12047,2008,A1 Location in patent:Page/Page column 20-21