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ChemicalBook CAS DataBase List (S)-(-)-1-(1-Naphthyl)ethylamine
10420-89-0

(S)-(-)-1-(1-Naphthyl)ethylamine synthesis

8synthesis methods
Using enzymes, particularly Candida Antarctic Lipase B, as catalysts, and utilizing the different transesterification rates of 1-(1-naphthyl)ethylamines of different chiralities, (R)-1-(1-naphthyl)ethylamine is esterified, while (S)-(-)-1-(1-naphthyl)ethylamine is retained. And then (S)-(-)-1-(1-naphthyl)ethylamine can be obtained by separation .
-

Yield:94 % ee

Reaction Conditions:

with ammonia in toluene at 87; under 2250.23 Torr; for 5 h;

Steps:

4

Aqueous ammonia (30%, 27.7 ml) was added to a Parr reactor. The toluene solution of the product of stage 3 was added and the reactor was sealed and heated to 87°C at 3 bar and allowed to react for 5 hours. At the end of this time the pressure was released and the toluene solution was separated and then evaporated to dryness to yield the title product, (S)-l-naphthylethylamine, in 94% e.e. (S)-l-naphthylethylamine was assessed using the HPLC protocol as described in stage 1(a) where (S)-1-Naphthylethylamine eluted at 12.0 minutes and (R)-l-Naphthylethylamine eluted at 5.9 minutes.

References:

WO2004/110976,2004,A2 Location in patent:Page/Page column 22

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