Potassium Carbonate → HCID 86600248, compound

HRID 1243805Notes

Reaction equation

HRID 1243805 reaction equation
[N:1]([CH2:4][C@@H:5]([O:13]C(=O)C)[C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([CH3:12])[N:7]=1)=[N+:2]=[N-:3].C([O-])([O-])=O.[K+].[K+]>CO>[N:1]([CH2:4][C@H:5]([C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([CH3:12])[N:7]=1)[OH:13])=[N+:2]=[N-:3]

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 86600247HCID 86600247, compound

Product 1

HCID 86600248HCID 86600248, compoundYield 100.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Dissolved acetic acid (R)-2-azido-1-(6-methyl-pyridin-2-yl)-ethyl ester (2.20 g, 9.90 mmol) into 50 mL of MeOH. To this was added K2CO3 (1.50 g) and the heterogenous mixture stirred for 2 h. LC-MS analysis indicated completion of the reaction. The mixture was concentrated and 100 mL of H2O was added. The mixture was extracted with 2×100 mL of CH2Cl2, dried with MgSO4, filtered and concentrated to give 1.78 g of (R)-2-azido-1-(6-methyl-pyridin-2-yl)-ethanol. ee % >99.

Workup

  1. customcompletion of the reaction
  2. concentrationThe mixture was concentrated
  3. addition100 mL of H2O was added
  4. extractionThe mixture was extracted with 2×100 mL of CH2Cl2
  5. dry with materialdried with MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-b34e6281f1bf41f0a7e7a18795764a2b
Source dataset
uspto-grants-2006_10
Patent number
US07119102B2

Reaction notes

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