BATHE ANDREAS DR.,HELFERT BERND,ACKERMANN KARL-AUGUST,GOTTSCHLICH RUDOLF DR.,STEIN INGEBORG DR.,BUDAK JENS
申请号：
SI9931065
公开号：
SI1607090T1
申请日:
1999.04.16
申请国别(地区):
SI
年份:
2012
代理人:
摘要：
Production of N-methyl-N-[(1S)-1-phenyl-2-((3S)-3-hydroxypyrrolidino)ethyl]-2,2-diphenylacetamide (Ia) or N-methyl-N-[(1R)-1-phenyl-2-((3R)-3-hydroxypyrrolidino)ethyl]-2,2-diphenylacetamide (Ib) comprises (a) reacting the corresponding enantiomer of an N-substituted phenylglycine derivative with an optionally O-protected 3-hydroxypyrrolidine derivative, (b) reducing the product to convert the N-substituent to methyl and remove any protecting group, and (c) reacting with an activated diphenylacetic acid derivative. Production of N-methyl-N-[(1S)-1-phenyl-2-((3S)-3-hydroxypyrrolidino)ethyl]-2,2-diphenylacetamide (Ia) or N-methyl-N-[(1R)-1-phenyl-2-((3R)-3-hydroxypyrrolidino)ethyl]-2,2-diphenylacetamide (Ib) comprises (a) reacting the corresponding enantiomer of an N-substituted phenylglycine derivative of formula (II) with an optionally O-protected 3-hydroxypyrrolidine derivative of formula (III), (b) reducing the product of formula (IV), and (c) reacting the product of formula (V) with an activated diphenylacetic acid derivative of formula (VI) to give a product of formula (Ia/Ib): [Image] [Image] [Image] [Image] R : H, OR 1>； or SR 1>；； R 1>；A, aryl, heteroaryl, Si(R 3>；) 3 or COR 3>；； R 3>；H, A, aryl or heteroaryl； A : 1-6C alkyl； M : H, alkali(ne earth) metal, NH 4 or alkylammonium； R 2>；H, A, aryl, heteroaryl, Si(R 3>；) 3 or COR 3>；； R 4>；halogen, OA or OCOA. An independent claim is also included for compounds referred to as N-methyl-N-[(1S)-1-phenyl-2-((3S)-3-hydroxypyrrolidino)ethane] and N-methyl-N-[(1R)-1-phenyl-2-((3R)-3-hydroxypyrrolidino)ethane] useful as intermediates for (Ia) and (Ib). ACTIVITY : Antiinflammatory； analgesic； diuretic. MECHANISM OF ACTION : None given.
