Ethanolamine → (3-{2-[(2-Hydroxy-ethylamino)-methyl]-4-trifluoromethyl-phenoxy}-phenyl)-acetic acid

HRID 885244Notes

Reaction equation

HRID 885244 reaction equation
[CH:1]([C:3]1[CH:19]=[C:18]([C:20]([F:23])([F:22])[F:21])[CH:17]=[CH:16][C:4]=1[O:5][C:6]1[CH:7]=[C:8]([CH2:12][C:13]([OH:15])=[O:14])[CH:9]=[CH:10][CH:11]=1)=O.[CH2:24]([CH2:26][NH2:27])[OH:25].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(Cl)Cl>[OH:25][CH2:24][CH2:26][NH:27][CH2:1][C:3]1[CH:19]=[C:18]([C:20]([F:21])([F:22])[F:23])[CH:17]=[CH:16][C:4]=1[O:5][C:6]1[CH:7]=[C:8]([CH2:12][C:13]([OH:15])=[O:14])[CH:9]=[CH:10][CH:11]=1

Participants

5

Reactant 3

HCID 700EthanolamineHCID 5049666Sodium triacetoxyborohydrideHCID 58237662[3-(2-Formyl-4-trifluoromethyl-phenoxy)-phenyl]-acetic acid

Product 1

HCID 58237504(3-{2-[(2-Hydroxy-ethylamino)-methyl]-4-trifluoromethyl-phenoxy}-phenyl)-acetic acidYield 109.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

[3-(2-Formyl-4-trifluoromethyl-phenoxy)-phenyl]-acetic acid (0.12 g, 0.37 mmol), ethanolamine (0.02 mL, 0.37 mmol), and sodium triacetoxyborohydride (0.12 g, 0.56 mmol) were combined in CH2Cl2 (10 mL) and stilled for 2 hours. After work-up, 0.15 g of the desired product was obtained.

Sources & evidence

ORD record
ord-0b3fae92d8a2430196c49dfafbd54957
Source dataset
uspto-grants-2012_08
Patent number
US08242145B2

Reaction notes

Loading…