Enantiomer compositions of (1R,4S)-1-butyrylamino-4-(hydroxymethyl)-2-cyclopentene

US6137007A · kind A · utility

Assignee

• LONZA LTD · CH

Inventors

• Christine Bernegger · Münster, CH
• Eva Maria Urban · Visp, CH
• Olwen M. Birch · Naters, CH
• Knut Burgdorf · Ried-Brig, CH
• Frank Brux · Raron, CH
• Kay-Sara Etter · Niedergampel, CH
• Pierre Bossard · Onex, CH
• Walter Brieden · Glis, CH
• Laurent Duc · Chermignon, CH
• John Gordon · Naters, CH
• Colm O'Murchu · Visp, CH
• Yves Guggisberg · Sierre, CH

Key dates

• Filing date: Aug 13, 1999
• Grant date: Oct 24, 2000
• Expiry date: Aug 13, 2019

Classification

• Technology area (CPC C): Chemistry; Metallurgy
• CPC primary: C07C2601/10
• WIPO field: Organic fine chemistry
• WIPO sector: Chemistry

Abstract

A novel process for the preparation of (1S,4R)- or (1R,4S)-4-(2-amino-6-chloro-9H-purin-9-yl)-2-cyclopentene-1-methanol of the formulae ##STR1## is described. This entails in the first stage (.+-.)-2-azabicyclo[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.