1-Butanol → HCID 70976006, compound

HRID 455283Notes

Reaction equation

HRID 455283 reaction equation
[F:1][C:2]([F:23])([F:22])[CH2:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([N:11]2[CH2:15][C@@H:14]3[CH2:16][C@@:17]4([CH2:20][O:19]4)[CH2:18][N:13]3[C:12]2=[O:21])=[CH:7][CH:6]=1.[H-].[Na+].[CH2:26]([OH:30])[CH2:27][CH2:28][CH3:29]>>[CH2:26]([O:30][CH2:20][C@@:17]1([OH:19])[CH2:18][N:13]2[C:12](=[O:21])[N:11]([C:8]3[CH:7]=[CH:6][C:5]([O:4][CH2:3][C:2]([F:23])([F:1])[F:22])=[CH:10][CH:9]=3)[CH2:15][C@@H:14]2[CH2:16]1)[CH2:27][CH2:28][CH3:29]

Participants

4

Reactant 3

HCID 2631-ButanolHCID 24758Sodium hydrideHCID 86673578HCID 86673578, compound

Product 1

HCID 70976006HCID 70976006, compoundYield 24%

Procedure

To a stirred solution of (2S,7a′S)-2′-[4-(2,2,2-trifluoroethoxy)phenyl]tetrahydro-3′H-spiro[oxirane-2,6′-pyrrolo[1,2-c]imidazol]-3′-one (40 mg, 0.121 mmol) in butanol (5 mL) was added NaH (60% in oil, 7.3 mg, 0.18 mmol) and heated to reflux for 12 h. The reaction mixture quenched with water and extracted with ethyl acetate. The organic layer was washed with water and brine, dried over Na2SO4 and concentrated. The residue purified by column chromatography on silica eluting with ethyl acetate/hexane to yield 12 mg (24%) of the title compound as white solid. LC-MS: 403.0 [M+1]+.

Workup

  1. temperatureheated
  2. temperatureto reflux for 12 h
  3. customThe reaction mixture quenched with water
  4. extractionextracted with ethyl acetate
  5. washThe organic layer was washed with water and brine
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated
  8. customThe residue purified by column chromatography on silica eluting with ethyl acetate/hexane

Sources & evidence

ORD record
ord-07c2a49d543a4a16b5a83b98af442cfb
Source dataset
uspto-grants-2013_07
Patent number
US08497288B2

Reaction notes

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