Synthesis of ((3R,6R)-6-Methylpiperidin-3-yl)methanol via Biocatalytic Transamination and Crystallization-Induced Dynamic Resolution
John W.N.C. Huang Foen Chung
1
,
Benjamin Marcune
1
,
Hallena R Strotman
1
,
Rositza I Petrova
1
,
Jeffrey C Moore
1
,
Peter G. Dormer
1
1
Department of Process Chemistry, Merck Research Laboratories, Merck & Co., Inc., P.O. Box 2000, Rahway, New Jersey 07065, United States
|
Publication type: Journal Article
Publication date: 2015-09-28
scimago Q1
wos Q1
SJR: 0.865
CiteScore: 5.4
Impact factor: 3.5
ISSN: 10836160, 1520586X
Organic Chemistry
Physical and Theoretical Chemistry
Abstract
An asymmetric synthesis of orexin receptor antagonist MK-6096 piperidine core, ((3R,6R)-6-methylpiperidin-3-yl)methanol (3), is described. The target is synthesized in four steps and 40% overall yield from methyl vinyl ketone and diethyl malonate. The key operation is a practical crystallization-induced dynamic resolution for the conversion of a trans/cis mixture of lactam acid 17 into the desired trans-lactam acid salt in >95% de and 91% yield. The substrate lactam acid mixture was prepared via a solvent-free Michael reaction and a practical biocatalytic transamination process.
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15
Total citations:
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Citations from 2025:
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Huang Foen Chung J. W. et al. Synthesis of ((3R,6R)-6-Methylpiperidin-3-yl)methanol via Biocatalytic Transamination and Crystallization-Induced Dynamic Resolution // Organic Process Research and Development. 2015. Vol. 19. No. 10. pp. 1418-1423.
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Huang Foen Chung J. W., Marcune B., Strotman H. R., Petrova R. I., Moore J. C., Dormer P. G. Synthesis of ((3R,6R)-6-Methylpiperidin-3-yl)methanol via Biocatalytic Transamination and Crystallization-Induced Dynamic Resolution // Organic Process Research and Development. 2015. Vol. 19. No. 10. pp. 1418-1423.
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TY - JOUR
DO - 10.1021/acs.oprd.5b00259
UR - https://doi.org/10.1021/acs.oprd.5b00259
TI - Synthesis of ((3R,6R)-6-Methylpiperidin-3-yl)methanol via Biocatalytic Transamination and Crystallization-Induced Dynamic Resolution
T2 - Organic Process Research and Development
AU - Huang Foen Chung, John W.N.C.
AU - Marcune, Benjamin
AU - Strotman, Hallena R
AU - Petrova, Rositza I
AU - Moore, Jeffrey C
AU - Dormer, Peter G.
PY - 2015
DA - 2015/09/28
PB - American Chemical Society (ACS)
SP - 1418-1423
IS - 10
VL - 19
SN - 1083-6160
SN - 1520-586X
ER -
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BibTex (up to 50 authors)
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@article{2015_Huang Foen Chung,
author = {John W.N.C. Huang Foen Chung and Benjamin Marcune and Hallena R Strotman and Rositza I Petrova and Jeffrey C Moore and Peter G. Dormer},
title = {Synthesis of ((3R,6R)-6-Methylpiperidin-3-yl)methanol via Biocatalytic Transamination and Crystallization-Induced Dynamic Resolution},
journal = {Organic Process Research and Development},
year = {2015},
volume = {19},
publisher = {American Chemical Society (ACS)},
month = {sep},
url = {https://doi.org/10.1021/acs.oprd.5b00259},
number = {10},
pages = {1418--1423},
doi = {10.1021/acs.oprd.5b00259}
}
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MLA
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Huang Foen Chung, John W.N.C., et al. “Synthesis of ((3R,6R)-6-Methylpiperidin-3-yl)methanol via Biocatalytic Transamination and Crystallization-Induced Dynamic Resolution.” Organic Process Research and Development, vol. 19, no. 10, Sep. 2015, pp. 1418-1423. https://doi.org/10.1021/acs.oprd.5b00259.