ChemicalBook CAS DataBase List (R)-(+)-1-Phenylethylamine

(R)-(+)-1-Phenylethylamine synthesis

5synthesis methods

Product Name:(R)-(+)-1-Phenylethylamine
CAS Number:3886-69-9
Molecular formula:C8H11N
Molecular Weight:121.18

67-56-1 Synthesis

67-56-1
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358629-51-3 Synthesis

(S)2-(2-Oxo pyrrolidin-1-yl)-Butiric acid methyl ester

358629-51-3
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3886-69-9
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Yield:358629-51-3 100%

Reaction Conditions:

Stage #1: (-)-(S)-alpha-ethyl-2-oxo-1-pyrrolidineacet-N-(+)-(R)-(1-phenylethyl)-amidewith sulfonic acid type-ion exchange resin;water in toluene;not specified; for 6 h;Heating / reflux;
Stage #2: methanolwith sulfonic acid type-ion exchange resin in water;toluene at 60; for 3 h;

Steps:

7

Example 7; (-)-(S)-alpha-ethyl-2-oxo-l-pyrrolidineacetic acid methyl ester.; In a 250 ml reactor equipped with mechanical stirring, thermometer and condenser, 2.5 g of (-)-(S)-alpha-ethyl-2-oxo-l-pyrrolidineacet-N-(+)-(R)-(l-phenylethyl)-amide (9.112 mmol, d.e.= 99.3%), 24.85 g (6 eq.) of p-toluensulfonic acid supported by polymeric matrix (30.00-60.00 mesh, 2.2 mmol/g) and 75 ml of toluene were charged. To the reaction mixture was added 0.660 ml (36.64 mmol) of water under stirring and mixture was heated up to reflux temperature. Reaction was monitored by HPLC and at complete conversion of starting material (about 6 h), mixture was cooled to 60⁰C temperature and 75 ml of methanol added. Reaction mixture was maintained at that temperature for 3 h up to complete formation of (-)-(S)-alpha- ethyl-2-oxo-l-pyrrolidineacetic acid methyl ester. Reaction mixture was permitted to cool and then it was filtered on gootch in order to separate the product from the resin. Resin was washed with methanol (2 x 75 ml) and organic phases were collected to give 365.1 g of a 0.462% organic solution of (-)-(S)-alpha-ethyl-2-oxo-l- pyrrolidineacetic acid methyl ester (1.69 g, 9.110 mmol, 100.0% yield) which was used in the following synthetic step. In order to recover (+)-(R)-(l-phenylethyl)-amine, resin was treated with 100 ml of 30% aqueous ammonia solution, 100 ml of methanol, 100 ml of 30% aqueous soda and again with 100 ml of methanol. Resin was then regenerated by washing with HCl 6 M (100 ml) and water up to neuter pH of the eluted phase. Finally, resin was washed with 100 ml of methanol and dried in oven at 50⁰C temperature under vacuum overnight.

References:

WO2008/12268,2008,A1 Location in patent:Page/Page column 20-21

98-86-2 Synthesis