| US 7,541,471 B2 | ||
| Synthesis of himbacine analogs | ||
| Tiruvettipuram K Thiruvengadam, Kendall Park, N.J. (US); Tao Wang, Springfield, N.J. (US); Jing Liao, Edison, N.J. (US); John S Chiu, Parsippany, N.J. (US); David Jieh-Shyh Tsai, Warren, N.J. (US); Hong-Chang Lee, Livingston, N.J. (US); Wenxue Wu, Princeton Junction, N.J. (US); and Xiaoyong Fu, Edison, N.J. (US) | ||
| Assigned to Schering Corporation, Keniworth, N.J. (US) | ||
| Filed on Jan. 12, 2006, as Appl. No. 11/330,935. | ||
| Claims priority of provisional application 60/643932, filed on Jan. 14, 2005. | ||
| Prior Publication US 2006/0173189 A1, Aug. 03, 2006 | ||
| Int. Cl. C07D 405/06 (2006.01) | ||
| U.S. Cl. 546—284.1 | 23 Claims |
1. A process for preparing Compound 1:
 (a) reducing a Compound 2A:
 wherein R2 is as defined above, and R3 is H, alkyl, cycloalkyl, aryl, arylalkyl or heteroaryl; R4 and R5 are each independently selected from the group consisting of H, alkyl, cycloalkyl, aryl, arylalkyl, and heteroaryl; or, R4 and R5, together with the carbon atom to which they are attached, form a 5- to 7- membered ring having from 0-3 heteroatoms as ring
members, to form 2B;
 followed by hydrolysis of 2B to yield a compound of formula 3:
 wherein R2 is as defined above;
(b) aminating Compound 3 to yield Compound 4:
 wherein R2 is as defined above, and R6 and R7 are each independently selected from the group consisting of H, alkyl, cycloalkyl, aryl, and heteroaryl;
(c) converting Compound 4 to Compound 5:
 wherein R1 and R2 are as defined above;
(d) converting Compound 5 to Compound 6:
 wherein R1 and R2 are as defined above; and
(e) converting Compound 6 to compound 1
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