HCID 86651685, compound → HCID 66896396, compound

HRID 337664Notes

Reaction equation

HRID 337664 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:17]=[C:18]([CH:21]=[O:22])[C:19]=1[CH3:20])[CH2:5][N:6]([CH:14]1[CH2:16][CH2:15]1)[C:7](=[O:13])[O:8][C:9]([CH3:12])([CH3:11])[CH3:10].[F:23][C:24]1[CH:25]=[C:26]([Mg]Br)[CH:27]=[CH:28][CH:29]=1>C1COCC1>[C:9]([O:8][C:7](=[O:13])[N:6]([CH2:5][C:4]1[CH:17]=[C:18]([CH:21]([C:28]2[CH:27]=[CH:26][CH:25]=[C:24]([F:23])[CH:29]=2)[OH:22])[C:19]([CH3:20])=[C:2]([Br:1])[CH:3]=1)[CH:14]1[CH2:15][CH2:16]1)([CH3:12])([CH3:11])[CH3:10]

Participants

4

Reactant 2

HCID 86651685HCID 86651685, compoundHCID 178505773HCID 178505773, compound

Product 1

HCID 66896396HCID 66896396, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a THF (0.13 M) solution of tert-butyl (3-bromo-5-formyl-4-methylbenzyl)cyclopropylcarbamate (1 eq.) from the previous step was added at 0° C. 3-fluorophenyl magnesium bromide (0.5 M in THF, 1.1 eq.). The resulting solution was warmed slowly to RT over 2 h before it was quenched with sat. aq. NH4Cl. The aqueous layer was separated and back-extracted with ether. The combined organic extracts were washed further with water and brine, dried over Na2SO4, filtered and the filtrate concentrated in vacuo. Further purification of the crude product by way of flash chromatography (SiO2, Hex→1:1 (v/v) Hex:EtOAc) afforded the title compound as a colorless oil.

Workup

  1. customwas quenched with sat. aq. NH4Cl
  2. customThe aqueous layer was separated
  3. extractionback-extracted with ether
  4. washThe combined organic extracts were washed further with water and brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationthe filtrate concentrated in vacuo
  8. customFurther purification of the crude product by way of flash chromatography (SiO2, Hex→1:1 (v/v) Hex:EtOAc)

Sources & evidence

ORD record
ord-e0829ae1e6df49f2a76415bfc82f3729
Source dataset
uspto-grants-2014_11
Patent number
US08889714B2

Reaction notes

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