Biomass derived furfural-based facile synthesis of protected (2S)-phenyl-3-piperidone, a common intermediate for many drugs

Abstract

An efficient synthetic route towards tosyl-protected (2S)-phenyl-3-piperidone, a common intermediate for many drugs, has been developed in 5 steps in 54% yield from biomass derived furfural. The synthetic utility of the piperidone core structure was demonstrated with the synthesis of a NK1 receptor antagonist.

Catalytic Synthesis of N‐(5‐Methylfurfuryl)aniline from Bio‐Derived Carbohydrates

“…Although this field is well‐recognized and sustainability idea is known, the primary requirement nowadays is to develop good procedures for organic synthesis with bio‐derived blocks and there is a keen interest in exploring chemical reactivity of biomass‐derived platform compounds . With developing a series of bio‐derived synthetic building blocks with different functional groups, the scope of application of biomass‐derived products was expanded, such as synthetic drugs, metal organic frameworks, and functional materials . Due to the carbonhydrates structure of lignocellulose, the bio‐derived products are mainly oxygen containing compounds .…”

Hydroxymethylation of Furfural to HMF with Aqueous Formaldehyde over Zeolite Beta Catalyst

“…In particular, 5-hydroxymethyl-2-furaldehyde (HMF) is the most important furaldehyde: it possesses two functionalities of formyl and hydroxyl groups on a furan ring at the second and fifth positions and this character enables various successive transformations to afford 2,5-furandicarboxylic acid [7,8], 2,5-diformylfuran [9,10], 2,5-bis(hydroxymethyl)furan (BHMF) [11,12], 2,5-dimethylfuran [13][14][15], 5-hydroxymethylfurfurylamine (HMFA) [16], 1,6-hexanediol [17], levulinic acid [18,19], aldol-adducts [20], and so on [21][22][23]. On the other hand, 2-furaldehyde (furfural), an abundant furaldehyde which is producible at the plant scale with a large quantity, has also permitted many conversions towards furoic acid [24,25], furfuryl alcohol [26,27], 2-methylfuran [28,29], furfuriyamine [30,31], 1,5-pentandiol [32,33], succinic acid [34], condensation products [35][36][37], cyclopentenones [38][39][40] and so on [41], as well as HMF reaction protocols. However, the number of possible derivatives of furfural and those impacts has been much less than those of HMF [1,6].…”

Synthesis of high value chemicals from biomass platform chemicals

“…Fossil fuels such as coal, petroleum and natural gas have served as cheap and easily accessible sources of energy and chemical feedstock for several centuries and they account for about 86% of the world's energy usage in 2014 1 . However, after more than 150 years of coal-based chemistry and 50 years of petroleum chemistry 2 , the world is now at a major crossroad to decide if it should continue indulging in the short-term riches of fossil fuels by turning a blind eye to the glaring limitations of fossil fuels.…”

“…The world is currently experiencing a dramatic increase in population since the 20 th century, marked by technological advances that reduces child mortality and raises life expectancy. It is projected that this upward momentum will persist to achieve a 1 BP Statistical Review of World Energy June 2015. http://www.bp.com/content/dam/bp/pdf/ energy-economics/statistical-review-2015/bp-statistical-review-of-world-energy-2015-full-report.pdf (accessed Oct 20, 2015 world population of 9.3 billion in 2050 from the 7 billion in 2011 3 . At the present rate of consumption, it is estimated that larger reserves of coal and petroleum are expected to deplete in less than 140 years and 50 years respectively 4 .…”

“…In addition, the use of fossil fuels such as coal results in emissions of sulphur oxides, nitrogen oxides and heavy metals, such as mercury and lead, which are detrimental to the well-being of mankind 10 . 1986 1988 1990 1992 1994 1996 1998 2000 2002 2004 2006 2008 The recent shale gas revolution 12 in the United States has seen the United States become the world's largest oil and gas producer 1 . As a result of this change in energy landscape, the price of crude oil dropped 50% to about US$50 per barrel at the time of writing.…”