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Synthesis and Stereochemistry of 7,9-Disubstituted 3-Azabicyclo[3.3.1]nonanes

✍ Scribed by Nemes, Peter ;Janke, Frank ;Scheiber, Pál

Publisher
John Wiley and Sons
Year
1993
Tongue
English
Weight
406 KB
Volume
1993
Category
Article
ISSN
0947-3440

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✦ Synopsis

Abstract

The azabicyclic endo compound 3 was synthesized by reaction of enamine 1 with 2‐benzoyl‐1,3‐dichloropropane (2). The thermodynamically more stable exo isomer 4 was obtained by epimerization of 3 with sodium methoxide. The reduction of 3 and 4 was carried out with different reducing agents. The syn/anti isomeric amino alcohols 7a/7b and 8a/8b were separated either by fractional crystallization of their fumarate salts or by column chromatography. The relative configurations at C‐7 and C‐9 and the conformations of the molecules were determined by chemical and/or NMR spectroscopic methods.

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Tertiäre 3-Oxa-7-azabicyclo[3.3.1]nonan-9-ole
✍ Rolf Haller; Ulrike Ashauer 📂 Article 📅 1985 🏛 John Wiley and Sons 🌐 English ⚖ 253 KB 👁 1 views

## Eingegangen am 6. Februar 1984 Von substituierten 3-0xa-7-azabicyclo[3.3.l]nonan-9-onen abgeleitete tertiare Alkohole werden durch Grignard-Reaktion der Ketone mit Propargylmagnesiumbromid erhalten. Die Stereoselektivitat dieser Reaktioncn ist sehr hoch. 'H-NMRund IR-Spektren werden diskutiert.