Tetrahydrofuran → 3-(5-Amino-1,3,4-oxadiazol-2-yl)pentan-3-ol

HRID 1988199Notes

Reaction equation

HRID 1988199 reaction equation
[CH2:1]([Mg]Br)[CH3:2].[NH2:5][C:6]1[O:10][C:9]([C:11]([O:13]CC)=O)=[N:8][N:7]=1.[CH2:16]1COC[CH2:17]1>>[NH2:5][C:6]1[O:10][C:9]([C:11]([OH:13])([CH2:1][CH3:2])[CH2:16][CH3:17])=[N:8][N:7]=1

Participants

4

Reactant 3

HCID 8028Tetrahydrofuran2×HCID 2756523Ethyl 5-amino-1,3,4-oxadiazole-2-carboxylateHCID 178418443HCID 178418443, compound

Product 1

HCID 574378393-(5-Amino-1,3,4-oxadiazol-2-yl)pentan-3-ol

Procedure

To a solution of ethyl magnesium bromide (200 mmol) in 300 mL of THF at 0° C. was added a suspension of ethyl 5-amino-1,3,4-oxadiazol-2-carboxylate (8.00 g, 50.9 mmol; Chemical Abstract, 1966, 64, 3558a) in THF. The reaction mixture was brought to rt and 30 min later quenched with NH4Cl. After extraction with EtOAc and drying over MgSO4, the solvent was removed. The crude product thus obtained was triturated, filtered and dried to yield the title compound.

Workup

  1. customlater quenched with NH4Cl
  2. extractionAfter extraction with EtOAc
  3. dry with materialdrying over MgSO4
  4. customthe solvent was removed
  5. customThe crude product thus obtained
  6. customwas triturated
  7. filtrationfiltered
  8. customdried

Sources & evidence

ORD record
ord-a93b1789eefe4102a66dfa592b1475df
Source dataset
uspto-grants-2009_06
Patent number
US07553973B2

Reaction notes

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