Methyl bromoacetate → Methyl[((trans)-2-{4-[(4-cyanobenzyl)oxy]phenyl}cyclopropyl)amino]acetate

HRID 1844246Notes

Reaction equation

HRID 1844246 reaction equation
Br[CH2:2][C:3]([O:5][CH3:6])=[O:4].[NH2:7][C@@H:8]1[CH2:10][C@H:9]1[C:11]1[CH:26]=[CH:25][C:14]([O:15][CH2:16][C:17]2[CH:24]=[CH:23][C:20]([C:21]#[N:22])=[CH:19][CH:18]=2)=[CH:13][CH:12]=1.CCN(C(C)C)C(C)C>CC#N>[CH3:6][O:5][C:3](=[O:4])[CH2:2][NH:7][C@@H:8]1[CH2:10][C@H:9]1[C:11]1[CH:12]=[CH:13][C:14]([O:15][CH2:16][C:17]2[CH:24]=[CH:23][C:20]([C:21]#[N:22])=[CH:19][CH:18]=2)=[CH:25][CH:26]=1

Participants

5

Reactant 3

HCID 60984Methyl bromoacetateHCID 81531DiisopropylethylamineHCID 671146174-({4-[(trans)-2-Aminocyclopropyl]phenoxy}methyl)benzonitrile

Product 1

HCID 123686250Methyl[((trans)-2-{4-[(4-cyanobenzyl)oxy]phenyl}cyclopropyl)amino]acetateYield 44%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

A solution of methyl bromoacetate (0.08 mL, 0.91 mmol) in CH3CN (6 mL) was added, over a period of 15 min, to a solution of 4-({4-[(trans)-2-aminocyclopropyl]phenoxy}methyl)benzonitrile (0.22 g, 0.82 mmol) and DIPEA (0.28 mL, 1.64 mmol) in CH3CN (8 mL) at −10° C. The reaction was allowed to reach room temperature and stirred for 22 h. After removal of the solvent, the crude residue was purified by column chromatography on silica gel (2-5% MeOH/CH2Cl2) affording 0.12 g of methyl[((trans)-2-{4-[(4-cyanobenzyl)oxy]phenyl}cyclopropyl)amino]acetate [Rf=0.5 (5% MeOH/CH2Cl2), pale yellow oil, 44% yield].

Workup

  1. customto reach room temperature
  2. customAfter removal of the solvent
  3. customthe crude residue was purified by column chromatography on silica gel (2-5% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-8da2bba8f2d943ea8dfb61623c03be9c
Source dataset
uspto-grants-2015_02
Patent number
US08946296B2

Reaction notes

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