1991
DOI: 10.1021/jo00020a052
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Selective reduction of carboxylic acids into alcohols using sodium borohydride and iodine

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Cited by 144 publications
(41 citation statements)
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“…The last transformation proceeded well using a mild reducing reagent, isobutyl aluminum hydride, after the published protocol. 19) A similar method was used to prepare 2-(2-chlorothiazol-5yl)ethylamine.…”
Section: Resultsmentioning
confidence: 99%
“…The last transformation proceeded well using a mild reducing reagent, isobutyl aluminum hydride, after the published protocol. 19) A similar method was used to prepare 2-(2-chlorothiazol-5yl)ethylamine.…”
Section: Resultsmentioning
confidence: 99%
“…L L-Phenylalanine 4 was reduced to L L-phenylalaninol by reduction with sodium borohydride and iodine using a method developed by Kanth and Periasamy 11 and later optimized for a-amino acids by Meyers et al (Scheme 1). 12 The resultant b-aminoalcohol was reductively alkylated 13 with acetone and sodium borohydride to afford the N-isopropyl derivative 5, which was converted to its corresponding b-hydrazino-alcohol 6.…”
Section: Resultsmentioning
confidence: 99%
“…This was used earlier for selective reduction of different carboxylic acids [12]. The optimum conditions for this reaction were a three-fold excess of I 2 and heating at 40°C for 6 h. This practically completely converted starting 1 to the diol 6, which was isolated in 73% yield.…”
mentioning
confidence: 95%
“…The optimum conditions for this reaction were a three-fold excess of I 2 and heating at 40°C for 6 h. This practically completely converted starting 1 to the diol 6, which was isolated in 73% yield. Carrying out the reaction at room temperature gave a low conversion of the starting compound that was probably due to the formation of insoluble intermediates [12]. Increasing the reaction time produced in the reaction mixture the product of further reduction, tetraol 3.…”
mentioning
confidence: 99%