Efficient synthesis of 6-amino-2-thiaspiro[3,3]heptane hydrochloride

Lü, Yan; Wang, Jin; Guo, Jianyu; Tang, Yanhui; Zhang, Suxia; Tao, Jianwei; Xiong, Lei; Li, Xiujie; Luo, Jingyi

doi:10.1515/hc-2014-0210

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“…Compound 11 was converted into 3-(tert-butoxycarbonyl)-1,1bis(hydroxymethyl)aminocyclobutane (25) in 6 steps. After the treatment of 25 with methanesulfonyl chloride, the obtained dimethanesulfonate 26 was reacted with sodium sulfide giving rise to 6-(tert-butoxycarbonyl)amino-2-thiaspiro [3.3]heptane (27), which was further transformed into the desired 6-amino-2thiaspiro [3,3]heptane (28) hydrogen chloride salt after the acidic deprotection [37] (Scheme 5).…”

Section: Methodsmentioning

confidence: 99%

Recent synthesis of thietanes

Xu¹

2020

Beilstein J. Org. Chem.

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Thietanes are important aliphatic four-membered thiaheterocycles that are found in the pharmaceutical core and structural motifs of some biological compounds. They are also useful intermediates in organic synthesis. Various synthetic methods of thietanes have been developed, including inter- and intramolecular nucleophilic thioetherifications, photochemical [2 + 2] cycloadditions, ring expansions and contractions, nucleophilic cyclizations, and some miscellaneous methods. The recently developed methods provide some new strategies for the efficient preparation of thietanes and their derivatives. This review focuses on the synthetic methods to construct thietane backbones developed during 1966 to 2019.

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