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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 51, 2021 - Issue 24
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Articles

Thiamine hydrochloride as a recyclable organocatalyst for the efficient and chemoselective N-tert-butyloxycarbonylation of amines

Ajit P. Ingalea Department of Chemistry, Dada Patil College, Savitribai Phule Pune University, Karjat, Ahmednagar, IndiaCorrespondence[email protected]
ORCID Iconhttps://orcid.org/0000-0001-9940-052X
ORCID Icon,
Dnyaneshwar N. Garadb School of Chemistry, National University of Ireland Galway, Galway, IrelandORCID Iconhttps://orcid.org/0000-0002-2108-4763
ORCID Icon,
Dattatraya Ukalec Department of Chemistry, University of Oxford, Oxford, United KingdomORCID Iconhttps://orcid.org/0000-0002-2929-0078
ORCID Icon,
Nitin M. Thoratd Department of Chemistry, Maharaja Jivajirao Shinde College, Savitribai Phule Pune University, Shrigonda, Ahmednagar, IndiaORCID Iconhttps://orcid.org/0000-0003-2880-1523
ORCID Icon &
Sandeep V. Shindee Department of Chemistry, Pratibha Niketan College, Swami Ramanand Teerth Marathwada University, Nanded, IndiaORCID Iconhttps://orcid.org/0000-0002-0328-5692
ORCID Icon
Pages 3791-3804 | Received 27 Aug 2021, Published online: 27 Oct 2021
 
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Abstract

Thiamin hydrochloride promoted highly efficient and ecofriendly approach has been described for the chemoselective N-tert-butyloxycarbonylation of amines under solvent-free conditions at ambient temperature. The demonstrated approach has been applicable for the N-Boc protection of variety of aliphatic, aryl, heteroaryl amines. The chemoselective protection of amino group occurs in chiral amines and amino alcohol without racemization in high yield. Thiamin hydrochloride is stable, economical, easy to handle and environmentally friendly.

Graphical Abstract

Acknowledgments

The author API gratefully acknowledges the financial support from Planning and Development, Savitribai Phule Pune University, Pune under ASPIRE-Research Mentorship Program (18TEC001308) and DST-FIST Instrumentation Facility, Dada Patil College, Karjat.

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