Utilizing biocatalysis and a sulfolane-mediated reductive acetal opening to access nemtabrutinib from cyrene-Reference-Cited by-同舟云学术

Utilizing biocatalysis and a sulfolane-mediated reductive acetal opening to access nemtabrutinib from cyrene

Published:2023 Issue:2 Volume:25 Page:606-613
ISSN:1463-9262
Container-title:Green Chemistry
language:en
Short-container-title:Green Chem.

Author:

Kuhl Nadine¹^ORCID,Turnbull Ben W. H.¹^ORCID,Ji Yining²^ORCID,Larson Reed T.¹^ORCID,Shevlin Michael¹,Prier Christopher K.¹^ORCID,Chung Cheol K.¹^ORCID,Desmond Richard¹,Guetschow Erik²,He Cyndi Qixin³,Itoh Tetsuji¹,Kuethe Jeffrey T.¹,Newman Justin A.²^ORCID,Reibarkh Mikhail²,Rivera Nelo R.²,Shang Gao¹,Wang Zhixun¹,Zewge Daniel²^ORCID,Thaisrivongs David A.¹

Affiliation:

1. Process Research and Development, Merck & Co., Inc., Rahway, New Jersey 07065, USA

2. Analytical Research and Development, Merck & Co., Inc., Rahway, New Jersey 07065, USA

3. Computational and Structural Chemistry, Merck & Co., Inc., Rahway, New Jersey 07065, USA

Abstract

The development of a protecting group-free, 2-step synthesis of 5-amino-2-hydroxymethyltetrahydropyran 1a from biorenewable Cyrene™ is described which renders access to BTK-inhibitor nemtabrutinib (2) more efficient and sustainable.

Funder

Merck

Publisher

Royal Society of Chemistry (RSC)

Subject

Pollution,Environmental Chemistry

Link

http://pubs.rsc.org/en/content/articlepdf/2023/GC/D2GC04117K

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2. Synthesis of Novel Tetrahydropyran-Based Dipeptide Isosters by Overman Rearrangement of 2,3-Didehydroglycosides

3. Thermal Overman Rearrangement of a Glucal Derivative in a Tube Reactor on Pilot Plant Scale