2-Azidomethyl-6-[(tert-butyldimethylsilyloxy)methyl]pyridine → 2-Aminomethyl-6-[(tert-butyldimethylsilyloxy)methyl]pyridine

HRID 473223Notes

Reaction equation

HRID 473223 reaction equation
[N:1]([CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([CH2:11][O:12][Si:13]([C:16]([CH3:19])([CH3:18])[CH3:17])([CH3:15])[CH3:14])[N:6]=1)=[N+]=[N-]>CO.[Pd].NCCN>[NH2:1][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([CH2:11][O:12][Si:13]([C:16]([CH3:19])([CH3:18])[CH3:17])([CH3:14])[CH3:15])[N:6]=1

Participants

4

Reactant 1

HCID 866715132-Azidomethyl-6-[(tert-butyldimethylsilyloxy)methyl]pyridine

Product 1

HCID 668467232-Aminomethyl-6-[(tert-butyldimethylsilyloxy)methyl]pyridineYield 80.2%

Reagents, catalysts & solvents 2

HCID 11513808Pd/C(en)CatalystHCID 887MethanolSolvent

Procedure

A suspension of 2-azidomethyl-6-[(tert-butyldimethylsilyloxy)methyl]pyridine (2) (0.83 g, 2.98 mmol) and 5% Pd/C(en) (83.0 mg, 10 wt %) in MeOH (20 mL) was vigorously stirred for 5 hours at a room temperature under a hydrogen atmosphere. TLC was used to confirm there was no starting material in the reaction mixture. Then, the catalyst was removed by suction filtration with a kiriyama funnel. The filtrate was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (CHCl3:MeOH=30:1 to 10:1) to give 2-aminomethyl-6-[(tert-butyldimethylsilyloxy)methyl]pyridine (3) (603 mg, 80%) as a yellow oil.

Workup

  1. customThen, the catalyst was removed by suction filtration with a kiriyama funnel
  2. customThe filtrate was evaporated under reduced pressure
  3. customThe residue was purified by silica gel column chromatography (CHCl3:MeOH=30:1 to 10:1)

Sources & evidence

ORD record
ord-706b3643cbae439a9dde7df6ab9d9b98
Source dataset
uspto-grants-2014_01
Patent number
US08633304B2

Reaction notes

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