𝔖 Bobbio Scriptorium
✦   LIBER   ✦

Synthesis of (R)- and (S)-amphetamine-d3 from the corresponding phenylalanines

✍ Scribed by Joseph Gal

Publisher
John Wiley and Sons
Year
1977
Tongue
French
Weight
297 KB
Volume
13
Category
Article
ISSN
0022-2135

No coin nor oath required. For personal study only.

✦ Synopsis

Abstract

The synthesis of (R)‐(−)‐ and (S)‐(+)‐2‐amino‐1‐phenylpropane‐3,3,3‐d~3~ via a modification of a published procedure for the unlabelled compounds is described. The preparation of the (S)enantiomer involved in the first step the reduction of D‐phenyl‐alanine to (R)‐2‐amino‐3‐phenyl‐1‐propanol–1,1‐d~2~ with lithium aluminum deuteride. The reduction product was treated with p‐toluenesulfonyl chloride to give (R)‐3‐phenyl–2‐(4‐toluenesulfamoyl)propyl–1,1‐d~2~ 4‐toluenesulfonate, which was reduced with lithium aluminum deuteride to (S)‐N‐(1‐methyl‐d^3^‐2‐phenethyl)‐4‐toluenesulfonamide. The latter compound was cleaved to (S)‐(+)‐2‐amino‐1‐phenylpropane‐3,3,3‐d~3~ using naphthalene anion radical. The overall yield in the sequence was 32.8%, the isotopic purity of the product was 99%, and the enantiomeric purity > 99%. The methyl ester of the amino acid could also be used as starting material in the synthesis.

📜 SIMILAR VOLUMES

Synthesis of D3-sulpiride and its (R) an
Synthesis of D3-sulpiride and its (R) and (S) isomers
✍ M. Al-koutayni-rifai; G. Jamet; R. R. Kerr; L. Jung; J. C. Koffel 📂 Article 📅 1989 🏛 John Wiley and Sons 🌐 French ⚖ 419 KB

Racemic dg-sulpiride, (R)-(+)-dg-sulpiride and (S)-(-)-dg-sulpiride (with three deuterium atoms in the methoxy function ortho to the benzamide), as well as (R)-(+)-sulpiride and (S)-(-)-sulpiride were synthesized. The structures were characterized by melting points, IR, 1H-NMR, GC-MS and polarimetry

ChemInform Abstract: Short Practical Syn
ChemInform Abstract: Short Practical Synthesis of (3R,4R,5R,6R)-Tetrahydroxyazepane and (3S,4S,5S,6S)-Tetrahydroxyazepane from D- and L-chiro-Inositol, Respectively.
✍ Gavin F. Painter; Andrew Falshaw 📂 Article 📅 2010 🏛 John Wiley and Sons ⚖ 32 KB 👁 1 views

## Abstract ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable v

Synthesis of D3-metoclopramide
Synthesis of D3-metoclopramide
✍ G. Jamet; Robert R. Kerr; S. Staveris; L. Jung; J. C. Koffel 📂 Article 📅 1986 🏛 John Wiley and Sons 🌐 French ⚖ 346 KB