Process for the preparation of aminoalcohol derivatives and their further conversion to (1R,4S)-4-((2-amino-6-chloro-5-formamido-4-pyrimidinyl)-amino)-2-cyclopentenyl-1-methanol

US6723868B1 · kind B1 · utility

Assignee

• LONZA LTD · CH

Inventors

• Walter Brieden · Glis, CH
• Josef Schroer · Susten, CH
• Christine Bernegger-Egli · Uster, CH
• Eva Maria Urban · Visp, CH
• Michael Petersen · Visp, CH
• Jean-Paul Roduit · Grône, CH
• Katja Berchtold · Baltschieder, CH
• Holger Breitbach · Baltschieder, CH

Key dates

• Filing date: Nov 24, 1998
• Grant date: Apr 20, 2004
• Expiry date: Nov 24, 2018

Classification

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

Abstract

The invention relates to a novel process for the preparation of an aminoalcohol of the formula racemically or optically active, starting from 2-azabicyclo[2.2.1]hept-5-en-3-one, its further conversion to give the corresponding acyl derivative and its further conversion to (1S,4R)- or (1R,4S)-4-(2-amino-6-chloro-9H-purine-9-yl)-2-cyclopentenyl-1-methanol of the formulae In the latter synthesis, the aminoalcohol is converted into the corresponding D- or L-tartrate, which is then reacted with N-(2-amino-4,6-dichloropyrimidin-5-yl)formamide of the formula to give (1S,4R)- or (1R,4S)-4-[(2-amino-6-chloro-5-formamido-4-pyrimidinyl)amino]-2-cyclopentenyl-1-methanol of the formulae and then cyclized to give the end compounds.