(Dimethyl sulfide)trihydroboron → HCID 68463601, compound

HRID 505033Notes

Reaction equation

HRID 505033 reaction equation
C[O:2][C:3]([CH:5]1[CH2:8][CH2:7][CH:6]1[N:9]1[CH:13]=[C:12]([N+:14]([O-:16])=[O:15])[N:11]=[CH:10]1)=O.CSC.B>O1CCCC1>[N+:14]([C:12]1[N:11]=[CH:10][N:9]([CH:6]2[CH2:7][CH2:8][CH:5]2[CH2:3][OH:2])[CH:13]=1)([O-:16])=[O:15]

Participants

4

Reactant 2

HCID 12423031(Dimethyl sulfide)trihydroboronHCID 68465660HCID 68465660, compound

Product 1

HCID 68463601HCID 68463601, compoundYield 37.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of the 2-(4-Nitro-imidazol-1-yl)-cyclobutanecarboxylic acid methyl ester (2.640 g, 0.01105 mol), borane-dimethyl sulfide complex (1M in tetrahydrofuran) (33.2 mL, 0.0332 mol) and tetrahydrofuran (10 mL) was heated at reflux for 17 hours. The reaction was quenched by water. The volatile solvent was evaporated under reduced pressure. The residue was diluted with water and extracted with ethyl acetate three times. The combined extracts were washed with brine and dried over sodium sulfate. The solvent was then evaporated under reduced pressure to yield [2-(4-Nitro-imidazol-1-yl)-cyclobutyl]-methanol (0.825 g, 0.00419 mol) as a white solid. M+1=198.1.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 17 hours
  3. customThe reaction was quenched by water
  4. customThe volatile solvent was evaporated under reduced pressure
  5. additionThe residue was diluted with water
  6. extractionextracted with ethyl acetate three times
  7. washThe combined extracts were washed with brine
  8. dry with materialdried over sodium sulfate
  9. customThe solvent was then evaporated under reduced pressure

Sources & evidence

ORD record
ord-b321837634c24c5ebf66d4c2676b4544
Source dataset
uspto-grants-2010_08
Patent number
US07781435B2

Reaction notes

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