(R)-2-Amino-3-phenylpropanoic acid (D-Phenylalanine) to (S)-1-Phenylpropan-2-amine (D-Amphetamine)

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Query Query O

H

1. Query

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Date

1 reactions in Reaxys

2018-03-28 09h:30m:26s (EST)

OH

NH 2

H 2N

H

Search as: As drawn, No salts, No mixtures

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2018-03-28 09:32:05


O H

HO H 2N

H 2N H

Cl

H

Rx-ID: 15764852 View in Reaxys 1/1 Yield

Conditions & References Reaction Steps: 5 1.1: 99 percent / lithium borohydride; trimethylsilyl chloride / tetrahydrofuran / 0.25 h / 20 °C 2.1: 95 percent / CHCl3 / 0 - 20 °C 3.1: 88 percent / iodine; triphenylphosphine polystyryl-supported; imidazole / CH2Cl2 / 2 h / Heating 4.1: 94 percent / N-Selectride / tetrahydrofuran / 1.5 h / 5 °C 5.1: trifluoroacetic acid / CH2Cl2 / 18 h / 20 °C 5.2: 91 percent / HCl / diethyl ether; CHCl3 With 1H-imidazole, lithium borohydride, chloro-trimethyl-silane, triphenylphosphine polystyryl-supported, iodine, sodium tri-sec-butylborohydride, trifluoroacetic acid in tetrahydrofuran, dichloromethane, chloroform, 1.1: Reduction / 2.1: Substitution / 3.1: Substitution / 4.1: Reduction / 5.1: Hydrolysis / 5.2: Addition Quagliato, Dominick A.; Andrae, Patrick M.; Matelan, Edward M.; Journal of Organic Chemistry; vol. 65; nb. 16; (2000); p. 5037 - 5042 View in Reaxys

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

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