Azide → HCID 58715502, compound

HRID 1243806Notes

Reaction equation

HRID 1243806 reaction equation
[N:1]([CH2:4][C@H:5]([C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([CH3:13])[N:8]=1)[OH:6])=[N+]=[N-].[N-]=[N+]=[N-]>[Pd].CCO>[NH2:1][CH2:4][C@H:5]([C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([CH3:13])[N:8]=1)[OH:6]

Participants

5

Reactant 2

HCID 33558AzideHCID 86600248HCID 86600248, compound

Product 1

HCID 58715502HCID 58715502, compoundYield 94.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

Suspended 10% Pd/C (0.50g) into 100 mL EtOH under Ar. To this was added (R)-2-azido-1-(6-methyl-pyridin-2-yl)-ethanol (3.57 g, 20.74 mmol). The reaction was placed under atm. H2 for 12 h. LC-MS analysis indicted some remaining azide. Recharge with H2 atmospher and stir an additional 12 h. LC-MS analysis indicated complete reaction. The mixture was filtered through a bed of celite. The celite was rinsed with 100 mL of EtOH. The filtrate was concentrated to give 2.99 g of (R)-2-amino-1-(6-methyl-pyridin-2-yl)-ethanol.

Workup

  1. customreaction
  2. filtrationThe mixture was filtered through a bed of celite
  3. washThe celite was rinsed with 100 mL of EtOH
  4. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-74a9861477924c0ba3093273cffbd9ff
Source dataset
uspto-grants-2006_10
Patent number
US07119102B2

Reaction notes

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