cis-4-Azido-2-benzhydryl-tetrahydropyran → cis-(2-Benzhydryl-tetrahydropyran-4-yl)-amine

HRID 606967Notes

Reaction equation

HRID 606967 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]=1

Participants

3

Reactant 1

HCID 86605345cis-4-Azido-2-benzhydryl-tetrahydropyran

Product 1

HCID 68717496cis-(2-Benzhydryl-tetrahydropyran-4-yl)-amineYield 100.7%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

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

  1. customfor 4 hr
  2. filtrationThe reaction mixture was filtered through a short bed of celite, and removal of the solvent

Sources & evidence

ORD record
ord-1847a1c64ecb4a12a02d0d15102beab6
Source dataset
uspto-grants-2011_03
Patent number
US07915433B2

Reaction notes

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