Tert-butyl[3-(7-benzyl-9-oxa-3,7-diazabicyclo[3.3.1]non-3-yl)propyl]carbamate → Tert-butyl[3-(9-oxa-3,7-diazabicyclo[3.3.1]non-3-yl)propyl]carbamate
Reaction equation
[C:1]([O:5][C:6](=[O:27])[NH:7][CH2:8][CH2:9][CH2:10][N:11]1[CH2:18][CH:17]2[O:19][CH:13]([CH2:14][N:15](CC3C=CC=CC=3)[CH2:16]2)[CH2:12]1)([CH3:4])([CH3:3])[CH3:2]>C(O)C.[OH-].[Pd+2].[OH-]>[C:1]([O:5][C:6](=[O:27])[NH:7][CH2:8][CH2:9][CH2:10][N:11]1[CH2:12][CH:13]2[O:19][CH:17]([CH2:16][NH:15][CH2:14]2)[CH2:18]1)([CH3:4])([CH3:2])[CH3:3]Participants
4
Procedure
tert-Butyl[3-(7-benzyl-9-oxa-3,7-diazabicyclo[3.3.1]non-3-yl)propyl]carbamate (0.85 g, 2.2 mmol; see Example 11 below) was dissolved in ethanol (10 mL). Palladium hydroxide (0.5 g) was then added and the reaction mixture was hydrogenated in Parr shaker under 2.45 bar pressure for 4 h. The reaction mixture was filtered and solvent concentrated under reduced pressure to give the title compound (0.71 g, 84%) as an orange solid.