(4-Amino-3'-chloro-biphenyl-3-yl)-cyclopropyl-methanone → 1-(4-Amino-3'-chloro-biphenyl-3-yl)-1-cyclopropyl-ethanol

HRID 413140Notes

Reaction equation

HRID 413140 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([Cl:14])[CH:9]=2)=[CH:4][C:3]=1[C:15]([CH:17]1[CH2:19][CH2:18]1)=[O:16].[CH3:20][Mg]Br>C1COCC1>[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([Cl:14])[CH:9]=2)=[CH:4][C:3]=1[C:15]([CH:17]1[CH2:18][CH2:19]1)([OH:16])[CH3:20]

Participants

4

Reactant 2

HCID 23509605(4-Amino-3'-chloro-biphenyl-3-yl)-cyclopropyl-methanoneHCID 178418573HCID 178418573, compound

Product 1

HCID 235096211-(4-Amino-3'-chloro-biphenyl-3-yl)-1-cyclopropyl-ethanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (4-amino-3′-chloro-biphenyl-3-yl)-cyclopropyl-methanone (0.67 g, 2.5 mmol) in anhydrous THF (10 mL) at −78° C. was added a solution of methylmagnesium bromide (3.0 M in diethyl ether, 2.5 mL, 7.5 mmol) under nitrogen. The reaction mixture was slowly warmed to rt, stirred under nitrogen for 12 hours, and quenched with a saturated aqueous ammonium chloride solution (40 mL). Ethyl acetate (50 mL) was added, the organic layer was separated, and dried (MgSO4). After removal of the solvent, the residue was purified via silica gel chromatography (hexane:ethyl acetate/7: 1) to afford 1-(4-amino-3′-chloro-biphenyl-3-yl)-1-cyclopropyl-ethanol as yellow oil: MS (EI) m/z 287/289 (M+).

Workup

  1. customquenched with a saturated aqueous ammonium chloride solution (40 mL)
  2. additionEthyl acetate (50 mL) was added
  3. customthe organic layer was separated
  4. dry with materialdried (MgSO4)
  5. customAfter removal of the solvent
  6. customthe residue was purified via silica gel chromatography (hexane:ethyl acetate/7: 1)

Sources & evidence

ORD record
ord-2657fcab4ebe46b8bb6d5fa3cc721bb4
Source dataset
uspto-grants-2003_05
Patent number
US06566358B2

Reaction notes

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