C - Chemistry – Metallurgy – 12 – P
Patent
C - Chemistry, Metallurgy
12
P
C12P 13/00 (2006.01) C07C 231/02 (2006.01) C07C 233/23 (2006.01) C07C 269/06 (2006.01) C07C 271/24 (2006.01) C07D 209/94 (2006.01) C07D 473/40 (2006.01) C12P 13/02 (2006.01) C12P 17/18 (2006.01) C12P 41/00 (2006.01)
Patent
CA 2237297
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 formula: Image is described. This entails in a first stage acylating (~)- 2-azabicyclo[2.2.1]hept-5-en-3-one of the formula: Image to give a (~)-2-azabicyclo[2.2.1]hept-5-en-3-one derivative of the general formula: Image in which R1 denotes C1-4-alkyl, C1-4-alkoxy, aryl or aryloxy, the latter being reduced in a second stage to give a cyclopentene derivative of the general formula: Image in which R1 has the stated meaning. The cyclopentene derivative V is then converted in a third stage biotechnologically into a (1R,4S)- or (1S,4R)-1-amino-4- (hydroxymethyl)-2-cyclopentene of the formula: Image the latter being converted in a fourth stage with N-(2- amino-4,6-dichloro-5-pyrimidinyl)formamide of the formula: Image into a (1S,4R)- or (1R,4S)-4-[(2-amino-6-chloro-5- formamido-4-pyrimidinyl)amino]-2-cyclopentene-1-methanol of the formula: Image Finally, the compound of forumula IX or X is cyclized in a fifth stage in a known manner to form the final product of formula I or II.
Bernegger Christine
Birch Olwen Mary
Bossard Pierre
Brieden Walter
Brux Frank
G. Ronald Bell & Associates
Lonza Ag
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