(S)-4-(1-Azido-2-(tert-butyldimethylsilyloxy)ethyl)pyridine → (S)-2-(tert-Butyldimethylsilyloxy)-1-(pyridin-4-yl)ethanamine

HRID 1623904Notes

Reaction equation

HRID 1623904 reaction equation
[N:1]([C@@H:4]([C:14]1[CH:19]=[CH:18][N:17]=[CH:16][CH:15]=1)[CH2:5][O:6][Si:7]([C:10]([CH3:13])([CH3:12])[CH3:11])([CH3:9])[CH3:8])=[N+]=[N-]>CO.[Pd]>[Si:7]([O:6][CH2:5][C@H:4]([C:14]1[CH:15]=[CH:16][N:17]=[CH:18][CH:19]=1)[NH2:1])([C:10]([CH3:13])([CH3:12])[CH3:11])([CH3:9])[CH3:8]

Participants

4

Reactant 1

HCID 86669655(S)-4-(1-Azido-2-(tert-butyldimethylsilyloxy)ethyl)pyridine

Product 1

HCID 67061097(S)-2-(tert-Butyldimethylsilyloxy)-1-(pyridin-4-yl)ethanamineYield 95.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

10% Pd/C (10 mg) was added to (S)-4-(1-azido-2-(tert-butyldimethylsilyloxy)ethyl)pyridine (58 mg, 0.208 mmol) in methanol. The reaction was degassed, and then charged with hydrogen. The reaction was stirred at room temperature overnight and filtered. The filtrate was concentrated to give the title compound (50 mg) without further purification.

Workup

  1. customThe reaction was degassed
  2. additioncharged with hydrogen
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-ce31dcd50948496bacd5e965ecfdedde
Source dataset
uspto-grants-2014_07
Patent number
US08778950B2

Reaction notes

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