Pyrrolidine → HCID 135492550, compound

HRID 1493028Notes

Reaction equation

HRID 1493028 reaction equation
Cl[CH2:2][C:3]1[N:7]=[C:6]([C:8]2[CH:13]=[C:12]([C:14]([CH3:17])([CH3:16])[CH3:15])[C:11]([OH:18])=[C:10]([C:19]([CH3:22])([CH3:21])[CH3:20])[CH:9]=2)[O:5][N:4]=1.[NH:23]1[CH2:27][CH2:26][CH2:25][CH2:24]1>CN(C=O)C>[CH3:15][C:14]([C:12]1[CH:13]=[C:8]([C:6]2[O:5][N:4]=[C:3]([CH2:2][N:23]3[CH2:27][CH2:26][CH2:25][CH2:24]3)[N:7]=2)[CH:9]=[C:10]([C:19]([CH3:22])([CH3:21])[CH3:20])[C:11]=1[OH:18])([CH3:17])[CH3:16]

Participants

4

Reactant 2

HCID 31268PyrrolidineHCID 135499967HCID 135499967, compound

Product 1

HCID 135492550HCID 135492550, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 0.5 g (0.002 mole) of 4-[3-(chloromethyl)-1,2,4-oxadiazol-5-yl]-2,6-bis(1,1-dimethylethyl)phenol and 0.4 g (0.006 mole) of pyrrolidine in DMF (10 ml) is stirred at room temperature for three hours. The mixture is poured into ice water (50 ml) and extracted with ethyl acetate (3×25 ml). The organic phase is washed with water (3×40 ml), dried (anhydrous magnesium sulfate), and evaporated, leaving an oil. Purification by flash chromatography (silica gel, ethyl acetate/hexane elution) yields 0.4 g (73%) of analytically pure 2,6-bis(1,1-dimethylethyl)-4-[3-(1-pyrrolidinylmethyl)-1,2,4-oxadiazol-5-yl]phenol, mp 100°-102° C.

Workup

  1. extractionextracted with ethyl acetate (3×25 ml)
  2. washThe organic phase is washed with water (3×40 ml)
  3. dry with materialdried (anhydrous magnesium sulfate)
  4. customevaporated
  5. customleaving an oil
  6. customPurification
  7. washby flash chromatography (silica gel, ethyl acetate/hexane elution)

Sources & evidence

ORD record
ord-a17f735e619b4af989140b3b50cf5414
Source dataset
uspto-grants-1994_12
Patent number
US05376670

Reaction notes

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