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. Author manuscript; available in PMC: 2011 Jun 4.
Published in final edited form as: J Org Chem. 2010 Jun 4;75(11):3587–3599. doi: 10.1021/jo1003778

Table 5.

cis to trans Epimerization of 1-(4’-nitro)-tetrahydro-β-carboline 7h under the conditions of Hamaker.34

graphic file with name nihms201035t3.jpg

Ethanolic HCl Time 7h
%
8h
%
15
%
saturated solution 3 h 90 10 < 1a
10 h c ND ND ND

1:2 dilution with
EtOH
2 d 60 40 < 1 b
4 d 25 75 < 1 b
a

Analyzed by 1H NMR;

b

by TLC;

c

decomposition occurred.