cis-4-Azido-2-benzhydryl-tetrahydropyran → cis-(2-Benzhydryl-tetrahydropyran-4-yl)-amine
Reaction equation
[N:1]([C@H:4]1[CH2:9][CH2:8][O:7][C@@H:6]([CH:10]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH2:5]1)=[N+]=[N-]>[Pd]>[CH:10]([C@H:6]1[CH2:5][C@@H:4]([NH2:1])[CH2:9][CH2:8][O:7]1)([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1Participants
3
Reactant 1
Product 1
Reagents, catalysts & solvents 1
Procedure
Cis-4-azido-2-diphenylmethyltetrahydropyran 5a (0.23 g, 0.78 mmol) was hydrogenated (60 psi) in the presence of 10% Pd—C (0.02 g, 10% wt) for 4 hr. The reaction mixture was filtered through a short bed of celite, and removal of the solvent afforded 0.21 g (quantitative yield) of product. This product was pure enough to continue to the next reaction step.
Workup
- customfor 4 hr