[49805-30-3]  · C6H7NO  · 2-Azabicyclo[2.2.1]hept-5-en-3-one  · (MW 109.13) (±)

[61865-48-3] (1R)

[79200-56-9] (1S)


(building block for the synthesis of carbocyclic nucleosides, GABA inhibitors, etc.)

Physical Data: mp 55-57 °C; bp 102-106 °C/0.25 mmHg.

Solubility: sol H2O, MeOH, CH2Cl2.

Form Supplied in: off-white solid.

Preparative Methods: from reaction of Cyclopentadiene with either sulfonyl cyanides1,2 or Chlorosulfonyl Isocyanate.3 Both enantiomers can be obtained via enzymic kinetic resolution of the racemate.4

2-Azabicyclo[2.2.1]hept-5-en-3-one (1) has been used as a building block for the synthesis of an array of compounds with potential pharmacological applications. Either enantiomer of cis-3-aminocyclopentanecarboxylic acid (2) is accessible from a single enantiomer of (1) (eq 1). Compound (2) has been shown to act as an agonist at the g-aminobutyric acid (GABA) receptor.5

The (1R,4S) enantiomer ((-)-1) has been used for the preparation of the carbocyclic nucleoside (-)-carbovir (3) (eq 2),6 which has been shown to have similar activity against HIV (RF strain) as AZT (Zidovudine).

Treatment of (1) with Potassium Monoperoxysulfate (oxone) gave an 80% yield of the exo-epoxide (4) (eq 3), which is of potential use for the preparation of carbocyclic analogs of 2-or 3-deoxyribofuranosylamines.

1. Daluge, S; Vince, R. JOC 1978, 43, 2311.
2. Griffiths, G.; Previdoli, F. Eur. Patent 508 352 (CA 1993, 118, 59 591).
3. Malpass, J. R.; Tweddle, N. J. JCS(P1) 1977, 874.
4. Taylor, S. J. C.; Sutherland, A. G.; Lee, C.; Wisdom, R.; Thomas, S.; Roberts, S. M.; Evans, C. CC 1990, 1120.
5. Evans, C.; McCague, R.; Roberts, S. M.; Sutherland, A. G. JCS(P1) 1991, 656.
6. Evans, C. T.; Roberts, S. M.; Shoberu, K. A.; Sutherland, A. G. JCS(P1), 1992, 589.
7. Legraverend, M.; Bisagni, E.; Huel, C. JHC, 1989, 26, 1881.

Gareth J. Griffiths

Lonza, Visp, Switzerland

Copyright 1995-2000 by John Wiley & Sons, Ltd. All rights reserved.