2-Aminoindan hydrochloride → {3-[2-(Indan-2-ylaminomethyl)-4-trifluoromethyl-phenoxy]-phenyl}-acetic acid methyl ester

HRID 1969056Notes

Reaction equation

Cl.[NH2:2][CH:3]1[CH2:11][C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4]1.C([O-])(=O)C.[Na+].[CH3:17][O:18][C:19](=[O:40])[CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[C:23]([O:27][C:28]2[CH:33]=[CH:32][C:31]([C:34]([F:37])([F:36])[F:35])=[CH:30][C:29]=2[CH:38]=O)[CH:22]=1.C([BH3-])#N.[Na+]>CO>[CH3:17][O:18][C:19](=[O:40])[CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[C:23]([O:27][C:28]2[CH:33]=[CH:32][C:31]([C:34]([F:36])([F:35])[F:37])=[CH:30][C:29]=2[CH2:38][NH:2][CH:3]2[CH2:11][C:10]3[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=3)[CH2:4]2)[CH:22]=1

Participants

Conditions

Temperature: 50 °C

Procedure

To 2-aminoindan hydrochloride (0.253 g, 1.49 mmol) in MeOH (2 mL) was added sodium acetate (0.122 g, 1.49 mmol), and the mixture was heated with a heating gun for 2 minutes. [3-(2-Formyl-4-trifluoromethyl-phenoxy)-phenyl]-acetic acid methyl ester (0.420 g, 1.24 mmol) in MeOH was added, followed by sodium cyanoborohydride (0.140 g, 2.23 mmol), and the reaction was stirred at room temperature for 2 hours and at 50° C. for 2 hours. After cooling to room temperature, the mixture was partitioned between EtOAc and saturated aqueous NaHCO3, and the aqueous layer was separated and extracted twice with EtOAc. The combined organic layers were dried and concentrated to give the title compound.

Workup

temperaturethe mixture was heated with a heating gun for 2 minutes
temperatureAfter cooling to room temperature
customthe mixture was partitioned between EtOAc and saturated aqueous NaHCO3
customthe aqueous layer was separated
extractionextracted twice with EtOAc
customThe combined organic layers were dried
concentrationconcentrated

Sources & evidence

ORD record: ord-f272b0d65efe480fb66d45a72f4d9030
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08426449B2

Reaction notes

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