Claims
- 1. A method for making a compound of Formula I ##STR17## wherein R.sup.1 is F, Cl, or C.sub.1 -C.sub.3 fluoroalkoxy and R.sup.2 is C.sub.1 -C.sub.3 alkyl; comprising
- (a) reacting a compound of Formula IV ##STR18## wherein R.sup.1 is F, Cl, or C.sub.1 -C.sub.3 fluoroalkoxy,
- R.sup.2 is C.sub.1 -C.sub.3 alkyl, and
- R.sup.3 is the protecting group CO.sub.2 CH.sub.2 (C.sub.6 H.sub.5); with di(C.sub.1 -C.sub.3 alkoxy)methane in the presence of a Lewis acid, to form a compound of Formula V ##STR19## (b) hydrogenating the compound of Formula V to make a compound of Formula VI ##STR20## wherein R.sup.1 is F, Cl, or C.sub.1 -C.sub.3 fluoroalkoxy and R.sup.2 is C.sub.1 -C.sub.3 alkyl; and
- (c) reacting the compound of Formula VI with a compound of Formula VII ##STR21##
CROSS-REFERENCE TO RELATED APPLICATIONS
This application is a divisional of application Ser. No. 09/165,651 filed Oct. 2, 1998, now U.S. Pat. No. 6,018,071, which is a divisional of application Ser. No. 08/727,607, filed Oct. 16, 1996, now U.S. Pat. No. 5,869,657 which is a continuation of PCT/US95/04321 filed Apr. 17, 1995, which is, in-turn, a continuation-in-part application of application Ser. No. 08/230,568 filed Apr. 20, 1994, now abandoned, and application Ser. No. 08/298,909 filed Aug. 31, 1994, now abandoned.
US Referenced Citations (3)
Number |
Name |
Date |
Kind |
3755453 |
Rosenthal et al. |
Aug 1973 |
|
3950367 |
Botta |
Apr 1976 |
|
4489074 |
Brown et al. |
Dec 1984 |
|
Foreign Referenced Citations (4)
Number |
Date |
Country |
0192150 |
Aug 1986 |
EPX |
129624 |
Apr 1986 |
PLX |
WO 9211249 |
Jul 1992 |
WOX |
WO 9220682 |
Nov 1992 |
WOX |
Non-Patent Literature Citations (4)
Entry |
Masui et al, New Methods and Reagents in Organic Synthesis. 75., Tetrahedron Letters, vol. 29, No. 23, 2835-2838, 1988 Oxford GB. |
Padwa et al., Involvement of Enol Tautomers in the Photosiomerization of 3-Substituted Isochromanoes, Journal of the American Chemical Society, vol. 98, No. 18, 5581-5590, Dec. 1975. |
T. Girija et al., Synthetic Investigations on Illudinine: a new synthesis of methyl 8-methoxy-2,2-dimethyl-7-oxo-1,2,3,5,6,7-hexahydro-s-indacene-4-carboxylate, Journal of the Chemical Society, No. 6, 1467-1471, Jun. 1991. |
Schulze, W., Chemical Abstract, Abstract No. 112:179779, with the reaction involving 126280-47-5 and 110-91-8 as searched in CASEREACT (1989). |
Divisions (2)
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Number |
Date |
Country |
Parent |
165651 |
Oct 1998 |
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Parent |
727607 |
Oct 1996 |
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Continuations (1)
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Number |
Date |
Country |
Parent |
PCTUS9504321 |
Apr 1995 |
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Continuation in Parts (1)
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Number |
Date |
Country |
Parent |
230568 |
Apr 1994 |
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