ChemicalBook CAS DataBase List (R)-(+)-1-(1-Naphthyl)ethylamine

(R)-(+)-1-(1-Naphthyl)ethylamine synthesis

9synthesis methods

Product Name:(R)-(+)-1-(1-Naphthyl)ethylamine
CAS Number:3886-70-2
Molecular formula:C12H13N
Molecular Weight:171.24

There are three main methods for preparing (R)-(+)-1-(1-Naphthyl)ethylamine: (1) Enzymatic separation method; (2) Chemical separation method, with the following separation agents used: chiral aspartic acid, chiral α-hydroxy naphthoic acid, protective chiral glycerol derivatives, and chiral tartaric acid; (3) Dissymmetric synthesis, etc. Using dissymmetric synthesis as an example, obtain Chiral Amine to prochiral ketone oxime through asymmetric catalytic hydrogenation reduction, method adopts ammonium formiate to reduce by 1-(1-naphthyl) acetophenone oxime, at chlorine { [(1R, 2R)-(-)-2-ammonia-1,2-Diphenethyl] (4-tolylsulfonyl) ammonia (p-isopropyl toluene) ruthenium (II)) catalyzer exist under, adopt polar solvent as dimethyl formamide, methyl alcohol, ethanol, n-propyl alcohol, Virahol, butanols, the one in the trimethyl carbinol.Catalytic asymmetric reduction single step reaction preparation (R)-(+)-1-(1-naphthyl) ethamine is carried out to 1-(1-naphthyl) acetophenone oxime.

42882-31-5 Synthesis

42882-31-5
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3886-70-2
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Yield:3886-70-2 88.3%

Reaction Conditions:

with p-chlorophenyl pentanoate;hydrogen in toluene at 55; under 75.0075 Torr; for 15 h;Enzymatic reaction;

Steps:

1.1 Preparation of (R) -l- (l-naphthyl) ethylamine:

In a 250 mL three-necked flask, mechanical stirring was slow,Toluene, 4 g of racemic naphthylethylamine, 5.2 g of acyl donor p-chlorophenol valerate, 1 g of Pd / LDH-SA and 0.4 g of lipaseNovozym 435, hydrogen pressure of 0.01MPa, 55 ° C under the conditions of reaction 15h, gas chromatography, Naphthylamine reaction completely, The catalyst (lipase and racemic catalyst) was removed by filtration and used in the next reaction, and the toluene solution was dissolved with sodium hydroxide(R) -amide; and the resulting (R) -amide was stirred at room temperature for 2 hours to remove p-chlorophenol, then dried and evaporated to dryness under reduced pressure to give2mol / L dilute hydrochloric acid hydrolysis 80 ° C 10h, then add ammonia to adjust pH> 10,0.5h after the dichloromethane burning extraction, drying, rotary steamTo give 3.538 (10-1- (1-naphthyl) ethylamine in a yield of 88.3%.

References:

CN104592037,2016,B Location in patent:Paragraph 0040