3-Methoxyphenol → (5R,7R)-7-(4-(3-(3-methoxyphenoxy)propyl)phenyl)-3-oxa-1-azaspiro[4.4]nonan-2-one

To a solution of (5R,7R)-7-(4-(3-hydroxypropyl)phenyl)-3-oxa-1-azaspiro[4.4]nonan-2-one (5.2 g, 18.89 mmol) in THF (150 mL) was added PS-triphenylphosphine 3 mmol/g (7.43 g, 28.3 mmol) followed by 3-methoxyphenol (2.457 mL, 22.66 mmol). After about 10 minutes a solution of di-tert-butylazodicarboxylate (5.22 g, 22.66 mmol) in THF (10 mL) was added. After about 4 hours the reaction mixture was filtered, rinsing with DCM and EtOAc. The filtrate was concentrated in vacuo and purified by chromatography on silica gel (DCM/EtOAc) to provide (5R,7R)-7-(4-(3-(3-methoxyphenoxy)propyl)phenyl)-3-oxa-1-azaspiro[4.4]nonan-2-one (5.1 g, 13.37 mmol, 70.8% yield) as a colorless solid.

1. filtrationAfter about 4 hours the reaction mixture was filtered
2. washrinsing with DCM and EtOAc
3. concentrationThe filtrate was concentrated in vacuo
4. custompurified by chromatography on silica gel (DCM/EtOAc)

ORDレコード

ord-0fb7772c3a1e44f7b5b775fa3a48aa5c

出典データセット

uspto-grants-2012_07

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US08217027B2