Diethyl Ether → HCID 22872664, compound

HRID 1780367Notes

Reaction equation

HRID 1780367 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([O:10][CH2:11][C@@H:12]2[CH2:15][CH2:14][N:13]2C(OC(C)(C)C)=O)[CH:6]=[N:7][C:8]=1[Cl:9])#N.[C:23]1([Mg]Br)[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.CC[O:33]CC>>[ClH:9].[C:1]([C:3]1[CH:4]=[C:5]([O:10][CH2:11][C@@H:12]2[CH2:15][CH2:14][NH:13]2)[CH:6]=[N:7][C:8]=1[Cl:9])(=[O:33])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

4

Reactant 3

HCID 3283Diethyl Ether2×HCID 22872671HCID 22872671, compoundHCID 178418255HCID 178418255, compound

Product 1

HCID 22872664HCID 22872664, compound

Procedure

The 5-cyano-6-chloro-3-(1-BOC-2-(S)-azetidinylmethoxy)pyridine of example 92a in anhydrous ether at 0° C. is treated with 1.5 equivalents of phenylmagnesium bromide in ether and stirring is maintained at 0° to 35° C. until the nitrile is largely consumed. The solvent is evaporated and the residue is treated with 2M aqueous potassium hydrogen sulfate to hydrolyze the intermediate imine. The solution is made basic with potassium carbonate and extracted with ethyl acetate. The combined extracts are dried (Na2SO4) and concentrated to a residue which is chromatographed (silica gel) to afford the title compound.

Workup

  1. customis largely consumed
  2. customThe solvent is evaporated
  3. additionthe residue is treated with 2M aqueous potassium hydrogen sulfate
  4. extractionextracted with ethyl acetate
  5. dry with materialThe combined extracts are dried (Na2SO4)
  6. concentrationconcentrated to a residue which
  7. customis chromatographed (silica gel)

Sources & evidence

ORD record
ord-48a8f40f72d24cfea0de76cb772d81d1
Source dataset
uspto-grants-1997_05
Patent number
US05629325

Reaction notes

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