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Stereoselective reduction via lithium borotritide: synthesis of 3 H‐labeled 2‐hydroxy‐N‐[(5‐hydroxy‐[5‐ 3 H]‐1,3,3‐trimethylcyclohexyl)methyl]‐5‐methylbenzamide
Author(s) -
Dischino Douglas D.,
Meanwell Nicholas A.,
Morimoto Hiromi,
Pearce Bradley C.,
Than Chit,
Torri Albert F.,
Williams Philip G.,
Yu KuoLong
Publication year - 1999
Publication title -
journal of labelled compounds and radiopharmaceuticals
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.432
H-Index - 47
eISSN - 1099-1344
pISSN - 0362-4803
DOI - 10.1002/(sici)1099-1344(199911)42:11<1061::aid-jlcr261>3.0.co;2-n
Subject(s) - chemistry , stereoselectivity , lithium (medication) , ketone , alcohol , high performance liquid chromatography , specific activity , organic chemistry , chromatography , enzyme , catalysis , medicine , endocrinology
3 H‐labeled 2‐hydroxy‐N‐[(5‐hydroxy‐[5‐ 3 H]‐1,3,3‐trimethyl‐cyclohexyl)methyl]‐5‐methylbenzamide, 1 , was prepared in one step by the reduction of the corresponding ketone with high specific activity LiBT 4 . The reduction was stereoselective yielding the desired cis alcohol in a ratio of >20 : 1. Purification of the compound was achieved on normal‐phase HPLC. The radiochemical purity of the final product was greater than 99.5% and the specific activity was 29 Ci/mmol. Copyright © 1999 John Wiley & Sons, Ltd.