CPC C07D 491/18 (2013.01) [C07D 471/18 (2013.01); C07D 491/22 (2013.01); C07D 498/18 (2013.01); C07D 498/22 (2013.01)] | 11 Claims |
1. A process of making a compound of formula (I):
or a pharmaceutically accepted salt thereof, wherein:
n is 1, 2, or 3;
X is selected from the group consisting of oxygen, NH, or sulfur;
Y is phenyl or pyridyl, optionally substituted by one or more substituents independently selected from the group consisting of C1-6alkyl, C1-4alkoxy, trifluoromethyl or halogen; and
Z is selected from the group consisting of C1-10 alkyl, C1-6 alkyl-NH—, and C1-10alkyl-O—, wherein said alkyl is unsaturated or saturated;
wherein the process comprises:
(A) contacting a compound of formula (I-A):
with a ruthenium catalyst in order to provide a compound of formula (I-B):
wherein:
Z′ for each occurrence is, independently, C1-4 alkyl, C1-2 alkyl-N (Boc)-, or C1-4 alkyl-O—;
(B) optionally contacting the compound of formula (I-B) with H2 and Wilkinson's catalyst to provide a compound of formula (I-C):
(C) contacting the compound of formula (I-B) or the compound of formula (I-C) with iron, and optionally contacting the resulting compound with trifluoroacetic acid, to provide the compound of formula (I).
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