4-(Trifluoromethyl)benzylamine → Ethyl 2-methyl-2-[2-methyl-4-({[4-(trifluoromethyl) benzyl]amino}methyl)phenoxy]propanoate

HRID 1269593Notes

Reaction equation

HRID 1269593 reaction equation
[CH:1]([C:3]1[CH:17]=[CH:16][C:6]([O:7][C:8]([CH3:15])([CH3:14])[C:9]([O:11][CH2:12][CH3:13])=[O:10])=[C:5]([CH3:18])[CH:4]=1)=O.[F:19][C:20]([F:30])([F:29])[C:21]1[CH:28]=[CH:27][C:24]([CH2:25][NH2:26])=[CH:23][CH:22]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(Cl)Cl>[CH3:14][C:8]([O:7][C:6]1[CH:16]=[CH:17][C:3]([CH2:1][NH:26][CH2:25][C:24]2[CH:23]=[CH:22][C:21]([C:20]([F:19])([F:29])[F:30])=[CH:28][CH:27]=2)=[CH:4][C:5]=1[CH3:18])([CH3:15])[C:9]([O:11][CH2:12][CH3:13])=[O:10]

Participants

5

Reactant 3

HCID 768044-(Trifluoromethyl)benzylamineHCID 5049666Sodium triacetoxyborohydrideHCID 18448413Ethyl 2-(4-formyl-2-methylphenoxy)-2-methylpropanoate

Product 1

HCID 18448415Ethyl 2-methyl-2-[2-methyl-4-({[4-(trifluoromethyl) benzyl]amino}methyl)phenoxy]propanoateYield 52.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of ethyl 2-(4-formyl-2-methylphenoxy)-2-methylpropanoate (0.563 g, 2.25 mmol) in CH2Cl2 (10 mL) under nitrogen at room temperature, was added 4-trifluoromethylbenzyl amine (0.34 mL, 2.37 mmol). The resulting solution was stirred for 30 minutes prior to addition of sodium triacetoxyborohydride (0.668 g, 3.15 mmol). After 18 h stirring the reaction mixture was quenched by cautious addition of sat. sodium bicarbonate aq. (30 mL) and extracted CH2Cl2 (2×50 mL). The organic solution was dried (MgSO4) and the solvent removed in vacuo. Purification by SPE (Silica, 20 g) eluting 9:1 cyclohexane:EtOAc afforded the title compound as a colourless oil (0.485 g).

Workup

  1. stirringAfter 18 h stirring the reaction mixture
  2. customwas quenched by cautious addition of sat. sodium bicarbonate aq. (30 mL)
  3. extractionextracted CH2Cl2 (2×50 mL)
  4. dry with materialThe organic solution was dried (MgSO4)
  5. customthe solvent removed in vacuo
  6. customPurification by SPE (Silica, 20 g)
  7. washeluting 9:1 cyclohexane

Sources & evidence

ORD record
ord-6d8c6d4dbe0540b0bac0f64c99a3b9c0
Source dataset
uspto-grants-2007_04
Patent number
US07199239B2

Reaction notes

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