Skip to main content
. Author manuscript; available in PMC: 2013 Jul 18.
Published in final edited form as: Tetrahedron Lett. 2012 May 12;53(29):3758–3762. doi: 10.1016/j.tetlet.2012.05.035

Table 1.

Screening of conditions for hydrogenolytic cleavage of the BOM group of 1.

graphic file with name nihms377344t1.jpg
entry catalyst conditions time (h) ratio (2/11) yield (%)
1 10% Pd/C MeOHa 6 20/80 >95
2 Pd black MeOHa 6 10/90 >95
3 Pd(OH)2 MeOHa 6 5/95 >95
4 PtO2 MeOHa 6 0/100 >95
5 10% Pd/C EtOHa 6 30/70 50
6 10% Pd/C EtOAca 6 95/5 <10
7 10% Pd/C iPrOHa 6 95/5 25
8 10% Pd/C iPrOH-H2O (10/1)a 6 100/0 25
9 10% Pd/C iPrOH-H2O (10/1) 50 psi 6 100/0 30~40
10 10% Pd/C iPrOH-H2O (10/1)a HCO2 NH4 (0.5%) 12 80/20 90
11 10% Pd/C iPrOH-H2O (10/1)a (CF3)2 CHOH (0.5%) 12 100/0 90
12 10% Pd/C iPrOH-H2O (10/1)a AcOH (0.5%) 6 100/0 90
13 10% Pd/C iPrOH-H2O (10/1)a HCO2H (0.5%) 6 100/0 >99
14 10% Pd/C iPrOH-H2O (10/1)a HCO2H (0.5%) 2 100/0 >99
15 10% Pd/C iPrOH-H2O (10/1) HCO2H (0.5%) 50 psi 0.5 100/0 >99
a

The reaction was conducted at 1atm H2 pressure.