Organic compounds -- part of the class 532-570 series – Organic compounds – Nitrogen attached directly or indirectly to the purine ring...
Patent
1998-05-06
2000-12-05
Berch, Mark L.
Organic compounds -- part of the class 532-570 series
Organic compounds
Nitrogen attached directly or indirectly to the purine ring...
560126, 564142, 564143, C07D47340, C07D48708, C07B23120, C07B23374, C07B23323
Patent
active
061568937
ABSTRACT:
A novel process for the preparation of (1S,4R)- or (1R,4S)-4-(2-amino-6-chloro-9H-purin-9-yl)-2-cyclo-pentene-1-methanol of the formulae ##STR1## is described. This entails in the first stage (.+-.)-2-aza-bicyclo[2.2.1]hept-5-en-3-one of the formula ##STR2## being acylated to give a (.+-.)-2-azabicyclo[2.2.1]hept-5-en-3-one derivative of the general formula ##STR3## in which R.sup.1 denotes C.sub.1-4 -alkyl, C.sub.1-4 -alkoxy, aryl or aryloxy, the latter being reduced in the second stage to give a cyclopentene derivative of the general formula ##STR4## in which R.sup.1 has the stated meaning, the latter then being converted in the third stage biotechnologically into the (1R,4S)- or (1S,4R)-1-amino-4-(hydroxymethyl)-2-cyclopentene of the formula ##STR5## the latter being converted in the fourth stage with N-(2-amino-4,6-dichloro-5-pyrimidinyl)formamide of the formula ##STR6## into the (1S,4R)- or (1R,4S)-4-[(2-amino-6-chloro-5-formamido-4-pyrimidinyl)amino]-2-cyclopente ne-1-methanol of the formulae ##STR7## and the latter being cyclized in the fifth stage in a known manner to the final product of the formula I or II.
REFERENCES:
patent: 5371282 (1994-12-01), Nohira et al.
Katagiri, Nucleosides & Nucleotides 15(1-3) 631-647, 1996.
Text version of USP 5270315, Dec. 1993.
Luis E. Martinez et al., "Highly Efficient and Enantioselective Synthesis of Carbocyclic Nucleoside Analogs Using Selective Early Transition Metal Catalysis", J. Org. Chem. 1996, vol. 61, pp. 7963-7966.
Michael T. Crimmins et al., "An Efficient Asymmetric Approach to Carbocyclic Nucleosides: Asymmetric Synthesis of 1259U89, a Potent Inhibitor of HIV Reverse Transcriptase", J. Org. Chem 1996, vol. 61, pp. 4192-4193.
Jeffrey A. Campbell et al., "Chirospecific Syntheses and Precursors of Cyclopentane and Cyclopentene Carbocyclic Nucleosides by [3+3]-Coupling and Transannular Alkyalation", J. Org. Chem. 1995, vol. 60, pp. 4602-4616.
Bernegger Christine
Birch Olwen Mary
Bossard Pierre
Brieden Walter
Brux Frank
Berch Mark L.
Lonza A.G.
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