(2S,4R,5R)-5-Azido-2-benzhydryl-tetrahydro-pyran-4-ol → (2S,4R,5R)-5-amino-2-benzhydryl-tetrahydro-pyran-4-ol

HRID 1897925Notes

Reaction equation

HRID 1897925 reaction equation
[N:1]([C@@H:4]1[CH2:9][O:8][C@H:7]([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)[CH2:6][C@H:5]1[OH:23])=[N+]=[N-]>CO.[Pd]>[NH2:1][C@@H:4]1[CH2:9][O:8][C@H:7]([CH:10]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH2:6][C@H:5]1[OH:23]

Participants

4

Reactant 1

HCID 11716531(2S,4R,5R)-5-Azido-2-benzhydryl-tetrahydro-pyran-4-ol

Product 1

HCID 11514718(2S,4R,5R)-5-amino-2-benzhydryl-tetrahydro-pyran-4-olYield 98%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

(2S,4R,5R)-5-Azido-2-benzhydryl-tetrahydro-pyran-4-ol (0.05 g, 0.18 mmol) dissolved in methanol (20 ml) was hydrogenated in the presence of 10% Pd/C (0.006 g). The mixture was filtered through a short bed of cellite, and evaporation of the solvent gave (2S,4R,5R)-5-amino-2-benzhydryl-tetrahydro-pyran-4-ol 0.05 g (97%, [α]D=(−)66, c=1, MeOH), which was pure enough for the next reaction.

Workup

  1. filtrationThe mixture was filtered through a short bed of cellite, and evaporation of the solvent

Sources & evidence

ORD record
ord-71d23364df1d4be8bd1b1a6354b7f347
Source dataset
uspto-grants-2013_08
Patent number
US08519159B2

Reaction notes

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