Deprotection of the methoxymethyl group on 3-spiro-2-oxindole under basic conditions

Atsuo Nakazaki; Kanako Iwakiri; Tomohiro Hirano; Takahiro Suzuki; Susumu Kobayashi

doi:10.1248/cpb.c13-00068

Deprotection of the methoxymethyl group on 3-spiro-2-oxindole under basic conditions

Chem Pharm Bull (Tokyo). 2013;61(5):587-91. doi: 10.1248/cpb.c13-00068.

Authors

Atsuo Nakazaki¹, Kanako Iwakiri, Tomohiro Hirano, Takahiro Suzuki, Susumu Kobayashi

Affiliation

¹ Faculty of Pharmaceutical Sciences, Tokyo University of Science, 2641 Yamazaki, Noda, Chiba 278-8510, Japan. nakazaki@agr.nagoya-u.ac.jp

PMID: 23649202
DOI: 10.1248/cpb.c13-00068

Abstract

Deprotection of a methoxymethyl (MOM) group on an oxindole nitrogen under basic conditions is demonstrated. The mechanisms of both the deprotection and the formation of N-methyloxindole were revealed by using deuterated NaOMe-MeOH in mechanistic studies.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Indoles / chemical synthesis*
Indoles / chemistry
Molecular Conformation
Spiro Compounds / chemistry*

Substances

Indoles
Spiro Compounds