Diethyl Ether → HCID 178425829, compound

HRID 2080945Notes

Reaction equation

HRID 2080945 reaction equation
[CH:1]1([N:4]([CH:15]2[CH2:20][CH2:19][CH:18]([CH2:21]C(OC)=O)[CH2:17][CH2:16]2)[C:5](=[O:14])[C:6]2[CH:11]=[CH:10][C:9]([CH3:12])=[CH:8][C:7]=2[F:13])[CH2:3][CH2:2]1.[CH3:26][Mg]Br.C([O:31][CH2:32][CH3:33])C>C1COCC1>[CH:1]1([N:4]([C@H:15]2[CH2:20][CH2:19][C@H:18]([CH2:21][C:32]([OH:31])([CH3:33])[CH3:26])[CH2:17][CH2:16]2)[C:5](=[O:14])[C:6]2[CH:11]=[CH:10][C:9]([CH3:12])=[CH:8][C:7]=2[F:13])[CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 24968896HCID 24968896, compoundHCID 178418573HCID 178418573, compound

Product 1

HCID 178425829HCID 178425829, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl 2-(4-(N-cyclopropyl-2-fluoro-4-methylbenzamido)cyclohexyl)acetate (0.075 g, 0.22 mmol) in THF (2 mL) was added methylmagnesium bromide, (3.0 M solution in diethyl ether, 0.43 ml, 1.3 mmol) at room temperature. After being stirred for 2 hours at room temperature, the reaction mixture was quenched with saturated NH4Cl (10 ml) and then extracted with EtOAc three times. The organic phase was dried over Na2SO4 and then concentrated in vacuo. The crude product was purified through silica gel chromatography eluting with 5% MeOH—CH2Cl2 and then 50% EtOAc-hexane. The desired product was obtained as a white solid (0.038 g). MS: 348 (M+1), C21H30FNO2.

Workup

  1. customthe reaction mixture was quenched with saturated NH4Cl (10 ml)
  2. extractionextracted with EtOAc three times
  3. dry with materialThe organic phase was dried over Na2SO4
  4. concentrationconcentrated in vacuo
  5. customThe crude product was purified through silica gel chromatography
  6. washeluting with 5% MeOH—CH2Cl2

Sources & evidence

ORD record
ord-bcbfb547374743a9b15d1409daf4e987
Source dataset
uspto-grants-2011_04
Patent number
US07932421B2

Reaction notes

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