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

HRID 1278654Notes

Reaction equation

HRID 1278654 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, organic layer was separated, and dried (MgSO4). After removal of solvent, the residue was purified via silica gel column (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. customorganic layer was separated
  4. dry with materialdried (MgSO4)
  5. customAfter removal of solvent
  6. customthe residue was purified via silica gel column (hexane:ethyl acetate/7:1)

Sources & evidence

ORD record
ord-439e9ae1a4294792b6794c76d84c9b9e
Source dataset
uspto-grants-2002_09
Patent number
US06444668B1

Reaction notes

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