Microwave-assisted synthesis of methyl (1S,2R,4S,5S)-7-aza-5- hydroxybicyclo[2.2.1]heptane-2-carboxylate through unexpected stereoselective substitution reaction

Satoru Onogi, Shuhei Higashibayashi, Hidehiro Sakurai

Research output: Contribution to journalArticle

2 Citations (Scopus)

Abstract

Methyl (1S,2R,4S,5R)-7-aza-5-bromo-bicyclo[2.2.1]heptane-2-carboxylate was synthesized in high yield in short time from methyl (1R,2S,4R,5R)-2-amino-4,5- dibromocyclohexanecarboxylate through intramolecular cycloamination under microwave-assisted conditions. The following substitution reaction by trifluoro-acetate anion also took place in microwave-assisted conditions to afford methyl (1S,2R,4S,5S)-7-aza-5-hydroxy-bicyclo[2.2.1]heptane-2-carboxylate. In the acyloxylation reaction, unusual endo-selectivity was observed owing to 7-azabicyclo[2.2.1]heptane skeleton.

Original languageEnglish
Pages (from-to)3710-3712
Number of pages3
JournalTetrahedron Letters
Volume53
Issue number29
DOIs
Publication statusPublished - 2012 Jul 18
Externally publishedYes

Fingerprint

Heptanes
Microwaves
Substitution reactions
Skeleton
Anions
Acetates
bicyclo(2.2.1)heptene
7-azabicyclo(2.2.1)heptane

Keywords

  • Azabicyclo[2.2.1]heptane
  • Cycloamination
  • Endo-selectivity
  • Hydroxylation
  • Microwave

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

Microwave-assisted synthesis of methyl (1S,2R,4S,5S)-7-aza-5- hydroxybicyclo[2.2.1]heptane-2-carboxylate through unexpected stereoselective substitution reaction. / Onogi, Satoru; Higashibayashi, Shuhei; Sakurai, Hidehiro.

In: Tetrahedron Letters, Vol. 53, No. 29, 18.07.2012, p. 3710-3712.

Research output: Contribution to journalArticle

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N2 - Methyl (1S,2R,4S,5R)-7-aza-5-bromo-bicyclo[2.2.1]heptane-2-carboxylate was synthesized in high yield in short time from methyl (1R,2S,4R,5R)-2-amino-4,5- dibromocyclohexanecarboxylate through intramolecular cycloamination under microwave-assisted conditions. The following substitution reaction by trifluoro-acetate anion also took place in microwave-assisted conditions to afford methyl (1S,2R,4S,5S)-7-aza-5-hydroxy-bicyclo[2.2.1]heptane-2-carboxylate. In the acyloxylation reaction, unusual endo-selectivity was observed owing to 7-azabicyclo[2.2.1]heptane skeleton.

AB - Methyl (1S,2R,4S,5R)-7-aza-5-bromo-bicyclo[2.2.1]heptane-2-carboxylate was synthesized in high yield in short time from methyl (1R,2S,4R,5R)-2-amino-4,5- dibromocyclohexanecarboxylate through intramolecular cycloamination under microwave-assisted conditions. The following substitution reaction by trifluoro-acetate anion also took place in microwave-assisted conditions to afford methyl (1S,2R,4S,5S)-7-aza-5-hydroxy-bicyclo[2.2.1]heptane-2-carboxylate. In the acyloxylation reaction, unusual endo-selectivity was observed owing to 7-azabicyclo[2.2.1]heptane skeleton.

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