Trimethylsilyldiazomethane → HCID 178501034, compound

HRID 1508523Notes

Reaction equation

HRID 1508523 reaction equation
[CH3:1][Si](C=[N+]=[N-])(C)C.[CH2:8]1[CH:13]([C:14]2[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][CH:15]=2)[CH2:12][CH2:11][CH:10]([C:21]([OH:23])=[O:22])[CH2:9]1>CO.C(O)(C(F)(F)F)=O>[Cl:20][C:17]1[CH:16]=[CH:15][C:14]([C@H:13]2[CH2:8][CH2:9][C@H:10]([C:21]([O:23][CH3:1])=[O:22])[CH2:11][CH2:12]2)=[CH:19][CH:18]=1

Participants

5

Reactant 2

HCID 167693TrimethylsilyldiazomethaneHCID 27357924-(4-Chlorophenyl)cyclohexane-1-carboxylic acid

Product 1

HCID 178501034HCID 178501034, compound

Reagents, catalysts & solvents 2

HCID 6422Trifluoroacetic acidCatalystHCID 887MethanolSolvent

Procedure

Trimethylsilyldiazomethane (15.71 ml, 31.4 mmol) was slowly added into a solution of (e)-4-(4-chlorophenyl)cyclohexanecarboxylic acid (3 g, 12.57 mmol) in MeOH (75 mL) at room temperature. LCMS indicated complete conversion in 1 hr. Added a few drops of TFA to quench the reaction. Volatiles were removed under reduced pressure. The resulting pot residue was purified by flash chromatography (SiO2, Biotage 65i cartridge). The column was eluted by an EtOAc/hexanes mixture (0% to 20%). Related fractions were pooled and evaporated to afford a white solid as the titled compound. LCMS calc.=252.09. found=253.20 (M+H)+.

Workup

  1. customin 1 hr
  2. customto quench
  3. customthe reaction
  4. customVolatiles were removed under reduced pressure
  5. customThe resulting pot residue was purified by flash chromatography (SiO2, Biotage 65i cartridge)
  6. washThe column was eluted by an EtOAc/hexanes mixture (0% to 20%)
  7. customevaporated

Sources & evidence

ORD record
ord-b5088267cf244cf58f20e1408f552f66
Source dataset
uspto-grants-2015_12
Patent number
US09221834B2

Reaction notes

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