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Sodium Azide → (S)-4-(1-Azido-2-(tert-butyldimethylsilyloxy)ethyl)pyridine

HRID 1623903
Notes
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Reaction equation

HRID 1623903 reaction equation
CS(O[C@H:6]([C:16]1[CH:21]=[CH:20][N:19]=[CH:18][CH:17]=1)[CH2:7][O:8][Si:9]([C:12]([CH3:15])([CH3:14])[CH3:13])([CH3:11])[CH3:10])(=O)=O.[N-:22]=[N+:23]=[N-:24].[Na+]>CN(C=O)C>[N:22]([C@@H:6]([C:16]1[CH:21]=[CH:20][N:19]=[CH:18][CH:17]=1)[CH2:7][O:8][Si:9]([C:12]([CH3:15])([CH3:14])[CH3:13])([CH3:11])[CH3:10])=[N+:23]=[N-:24]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 33557Sodium AzideHCID 86669654(R)-2-(tert-Butyldimethylsilyloxy)-1-(pyridin-4-yl)ethyl Methanesulfonate

Product 1

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

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
40 °C

Procedure

(R)-2-(tert-Butyldimethylsilyloxy)-1-(pyridin-4-yl)ethyl methanesulfonate was taken in DMF, and sodium azide (61.6 mg, 0.947 mmol) was added. The reaction mixture was warmed to 40° C., and stirred overnight. The solvent was evaporated, and the residue was purified by silica gel column chromatography to give the title compound as a colorless oil (58 mg). LCMS m/z=279.3 [M+H]+.

Workup

  1. customThe solvent was evaporated
  2. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-8dd79969845f4a189dfb5cd1c099b252
Source dataset
uspto-grants-2014_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08778950B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes