Sodium Hydroxide → 1-(5-(4-Chloro-3-(trifluoromethyl)phenyl)furan-2-yl)propan-2-amine

Temperature

0 °C

(E)-2-(4-chloro-3-(trifluoromethyl)phenyl)-5-(2-nitroprop-1-enyl)furan (2.58 g, 7.78 mmol) was mixed with diethyl ether (54 ml) and toluene (25 ml) and added drop wise to a cooled (−20° C.) solution of lithium aluminium hydride (2.5 g, 65.9 mmol) in diethyl ether (11 ml). The mixture was allowed to warm up to 0° C. and stirred for 3 h and then at RT for additional 1 h stirring. Then the mixture was cooled again and 2.5 ml of water was added at −30° C. and then 2.5 ml of 15% aqueous NaOH solution. An additional 7.5 ml of water was added and the solution was allowed to warm to RT. MgSO4 was added and the mixture was stirred and filtered, precipitate was washed with toluene and diethyl ether and the filtrate was evaporated to dryness. After CombiFlash purification with DCM:MeOH as eluent system, the pooled fractions afforded 1.13 g of the title compound. 1H-NMR (400 MHz; d6-DMSO): δ 1.01 (d, 3H), 2.63 (m, 2H), 3.11-3.15 (m, 1H) 6.28 (d, 1H), 7.07 (d, 1H), 7.68 (d, 1H), 7.87 (m, 1H), 7.95 (m, 1H).

1. additionadded drop wise to
2. stirringat RT for additional 1 h stirring
3. temperatureThen the mixture was cooled again
4. temperatureto warm to RT
5. stirringthe mixture was stirred
6. filtrationfiltered
7. washprecipitate was washed with toluene and diethyl ether
8. customthe filtrate was evaporated to dryness
9. customAfter CombiFlash purification with DCM

ORD record

ord-b47e29f393764537a1730cc08a5a07de

Source dataset

uspto-grants-2015_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08975254B2