HCID 70983650, compound → HCID 70983672, compound

HRID 2272660Notes

Reaction equation

HRID 2272660 reaction equation
[CH3:1][CH:2]1[CH2:7][CH:6]([C:8]([C:10]2[S:11][CH:12]=[CH:13][N:14]=2)=[O:9])[CH2:5][CH2:4][CH:3]1[C:15]([O:17][CH2:18][CH3:19])=[O:16].[CH3:20][Mg+].[Br-]>C1COCC1>[OH:9][C:8]([CH:6]1[CH2:5][CH2:4][CH:3]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH:2]([CH3:1])[CH2:7]1)([C:10]1[S:11][CH:12]=[CH:13][N:14]=1)[CH3:20]

Participants

4

Reactant 2

HCID 70983650HCID 70983650, compoundHCID 178418689HCID 178418689, compound

Product 1

HCID 70983672HCID 70983672, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-40 °C

Procedure

To a solution of ethyl 2-methyl-4-(1,3-thiazol-2-ylcarbonyl)cyclohexanecarboxylate (2.8 g, 10 mmol) in THF (28 mL) at −40° C. was added MeMgBr (3.0 M in THF, 4.0 mL, 12 mmol) at such a rate the internal temperature did not exceed −30° C. The reaction mixture was stirred for 15 minutes at −40° C., and was then quenched with saturated aqueous ammonium chloride (50 mL) and warmed to room temperature. EtOAc (20 mL) was added, the layers separated, and the aqueous layer was extracted a second time with EtOAc (50 mL). The organic layers were combined, dried over MgSO4, filtered, absorbed on silica, and purified by silica gel chromatography to afford ethyl 4-[1-hydroxy-1-(1,3-thiazol-2-yl)ethyl]-2-methylcyclohexanecarboxylate.

Workup

  1. customdid not exceed −30° C
  2. customwas then quenched with saturated aqueous ammonium chloride (50 mL)
  3. temperaturewarmed to room temperature
  4. additionEtOAc (20 mL) was added
  5. customthe layers separated
  6. extractionthe aqueous layer was extracted a second time with EtOAc (50 mL)
  7. dry with materialdried over MgSO4
  8. filtrationfiltered
  9. customabsorbed on silica
  10. custompurified by silica gel chromatography

Sources & evidence

ORD record
ord-a1bdfe85bf964f7f939d6a4ee4ab4bfc
Source dataset
uspto-grants-2015_09
Patent number
US09120785B2

Reaction notes

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