Potassium Carbonate → (R)-2-(6-Methoxy-[1,5]-naphthyridin-4-yl)oxirane

HRID 638997Notes

Reaction equation

HRID 638997 reaction equation
Br[CH2:2][C@@H:3]([C:5]1[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([O:15][CH3:16])[N:13]=2)[N:8]=[CH:7][CH:6]=1)[OH:4].C(=O)([O-])[O-].[K+].[K+]>CO>[CH3:16][O:15][C:12]1[N:13]=[C:14]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][CH:6]=[C:5]2[C@@H:3]1[CH2:2][O:4]1

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 23400264(R)-2-Bromo-1-(6-methoxy-[1,5]-naphthyridin-4-yl)ethanol

Product 1

HCID 23400263(R)-2-(6-Methoxy-[1,5]-naphthyridin-4-yl)oxiraneYield 92%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

(R)-2-Bromo-1-(6-methoxy-[1,5]-naphthyridin-4-yl)ethanol (4.8 g, 0.017 mol) in methanol (20 ml) was stirred with potassium carbonate (2.6 g, 0.019 mol) for 1 hour, then evaporated and chromatographed on silica gel (ethyl acetate-hexane-dichloromethane) to give a solid (3.14 g, 92%), (91% ee by chiral HPLC).

Workup

  1. customevaporated
  2. customchromatographed on silica gel (ethyl acetate-hexane-dichloromethane)

Sources & evidence

ORD record
ord-72ac8f1277f14964a647c8fdfdcd71f0
Source dataset
uspto-grants-2010_04
Patent number
US07691850B2

Reaction notes

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