Sodium cyanoborohydride → Methyl 2-(2-(3-trifluoromethylphenyl)-4-(1-(methylamino)ethyl)phenoxy)acetate

HRID 68599Notes

Reaction equation

HRID 68599 reaction equation
[C:1]([C:4]1[CH:15]=[CH:14][C:7]([O:8][CH2:9][C:10]([O:12][CH3:13])=[O:11])=[C:6]([C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([C:22]([F:25])([F:24])[F:23])[CH:17]=2)[CH:5]=1)(=O)[CH3:2].Cl.CN.[C:29]([BH3-])#[N:30].[Na+]>CO.C(OCC)(=O)C>[F:23][C:22]([F:25])([F:24])[C:18]1[CH:17]=[C:16]([C:6]2[CH:5]=[C:4]([CH:1]([NH:30][CH3:29])[CH3:2])[CH:15]=[CH:14][C:7]=2[O:8][CH2:9][C:10]([O:12][CH3:13])=[O:11])[CH:21]=[CH:20][CH:19]=1

Participants

6

Reactant 3

HCID 5003444Sodium cyanoborohydrideHCID 6364545Methylamine hydrochlorideHCID 66868647Methyl 2-(4-acetyl-2-(3-trifluoromethylphenyl)phenoxy)acetate

Product 1

HCID 67527946Methyl 2-(2-(3-trifluoromethylphenyl)-4-(1-(methylamino)ethyl)phenoxy)acetateYield 108.9%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of methyl 2-(4-acetyl-2-(3-trifluoromethylphenyl)phenoxy)acetate (17) (529 mg, 1.5 mmol, 1 eq) in MeOH (5 mL) was added methylamine hydrochloride (603 mg, 9.0 mmol, 6 eq) and sodium cyanoborohydride (93 mg, 1.5 mmol, 1 eq). The reaction mixture was stirred at room temperature for 8 days, diluted with ethyl acetate, washed with water, dried (Na2SO4), and concentrated in vacuo to give crude compound methyl 2-(2-(3-trifluoromethylphenyl)-4-(1-(methylamino)ethyl)phenoxy)acetate (18) as white solid (600 mg) which was carried directly to the next step.

Workup

  1. washwashed with water
  2. dry with materialdried (Na2SO4)
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-5f51b85f4e6b4536b8c64083c42dcfaf
Source dataset
uspto-grants-2014_09
Patent number
US08822467B2

Reaction notes

Loading…