Erratum: A practical synthesis of renin inhibitor MK-1597 (ACT-178882) via catalytic enantioselective hydrogenation and epimerization of piperidine intermediate (Journal of Organic Chemistry (2011) 76 (1062-1071) DOI: 10.1021/jo102070e)

Full text of DOI:10.1021/jo202488m

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A Practical Synthesis of Renin Inhibitor MK-1597 (ACT-178882) via
Catalytic Enantioselective Hydrogenation and Epimerization of
Piperidine Intermediate
Carmela Molinaro,* Scott Shultz, Amelie Roy, Stephen Lau, Thao Trinh, Remy Angelaud, Paul D. O’Shea,
Stefan Abele, Mark Cameron, Ed Corley, Jacques-Alexis Funel, Dietrich Steinhuebel, Mark Weisel,
and Shane Krska
J. Org. Chem. 2011, 76, 1062−1071. DOI: 10.1021/jo102070e.
Corrected scheme for Table 1:
K. P. M.; Dobbs, D. A.; Rautenstrauch, V. Angew. Chem., Int. Ed.
2001, 40, 914. (g) Dupau, P.; Bruneau, C.; Dixneuf, P. H. Adv.
Synth. Catal. 2001, 343, 331. (h) Tang, W.; Wu, S.; Zhang, X.
J. Am. Chem. Soc. 2003, 125, 9570. Reviews: (i) Genet, J. P. Acc.
Chem. Res. 2003, 36, 908. (j) Shultz, S. C.; Krska, S. K. Acc.
Chem. Res. 2007, 12, 1320. (k) Inter alia: Blaser, H. U.; Spindler,
F.; Thommen, M. Industrial Applications. In Handbook of Homo-
geneous Hydrogenation; de Vries, J. G., Elsevier, C. J., Eds.; Wiley-
VCH: New York, 2007; pp 1279−1324.
Procedure for microscale screening reactions in Table 1: A
1.5 mg/mL stock solution of (COD)Ru(Me-allyl)2 was pre-
pared in 1,2-dicholoroethane and then pipetted into a 1 mL
glass vial containing the desired phosphine ligand (0.42 mmol,
1.05 equiv). The solution was agitated, and 2.0 equiv (relative
to Ru) of HBF4·OEt2 (20 mM in 1,2-dichloroethane) was
added. The resultant solutions were agitated for 30 min and
evaporated to dryness. A stock solution of the ene ester 4a and
HBF4·OEt2 (at a ratio as determined in Table 1) was prepared
in the appropriate screening solvent. The concentration of this
stock solution was determined on the basis of achieving the
desired substrate to catalyst ratio as given in Table 1 and a fixed
addition of 150 μL to the 1 mL glass vial containing dried
catalyst. Hydrogenations were carried out at 500 psig of H2 and
for a duration of 18 h. Note: For entries 1−7 in Table 1, the
amount of HBF4·OEt2 is the molar amount relative to substrate 4a
and does not include acid added during catalyst preparation.
For previous work on precatalysts and catalysts in this area,
see: (a) Heiser, B.; Broger, E.A.; Crameri, Y. Tetrahedron:
Asymmetry 1991, 2, 51. (b) Schmid, R.; Broger, E. A.;
Cereghetti, M.; Crameri, Y.; Foricher, J.; Lalonde, M.; Muller,
R. K.; Scalone, M.; Schoettel, G.; Zutter, U. Pure Appl. Chem.
1996, 68, 131. (c) Currao, A.; Feiken, N; Macchioni, A; R.
Nesper, R.; Pregosin, P. S.; Trabesinger, G. G. Helv. Chim. Acta
1996, 79, 1587. (d) Wiles, J. A.; Lee, C. E.; McDonald, R.;
Bergens, S. H. Organometallics 1996, 15, 3782. (e) Dobbs, D.
A.; Vanhessche, K. P. M.; Brazi, E.; Rautenstrauch, V.; Lenoir,
J.-Y.; Genet, J.-P.; Wiles, J.; Bergens, S. H. Angew. Chem., Int.
Ed. 2000, 39, 1992. (f) Wiles, J. A.; Bergens, S. H.; Vanhessche,
Published: December 21, 2011
© 2011 American Chemical Society
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