Boron trifluoride → [4-(2-Heptylamino-ethyl)-phenyl]-methanol

To a stirred solution of N-heptyl-2-(4-hydroxymethyl-phenyl)-acetamide (5.6 mmol, 1.48 g) dissolved in tetrahydrofuran (15 mL) under a nitrogen atmosphere at 0° C. was added sodium borohydride (16.9 mmol, 639 mg) followed by the dropwise addition of boron trifluoride diethyletherate (22.5 mmol, 2.85 mL). The mixture was allowed to stir at room temperature for 11 hours. The reaction was quenched by the cautious addition of 2N HCl until gas evolution had ceased. The resulting mixture was refluxed for 45 minutes, cooled to room temperature and concentrated to a white solid. The solid was dissolved in water, then brought to pH 14 with 2N NaOH. The aqueous solution was extracted with diethyl ether (3×). The organic layers were combined, washed with brine (1×), dried over anhydrous sodium sulfate and concentrated to give [4-(2-heptylamino-ethyl)-phenyl]-methanol as a clear oil (1.37 g, 98%).

1. customThe reaction was quenched by the cautious addition of 2N HCl until gas evolution
2. temperatureThe resulting mixture was refluxed for 45 minutes
3. temperaturecooled to room temperature
4. concentrationconcentrated to a white solid
5. dissolutionThe solid was dissolved in water
6. extractionThe aqueous solution was extracted with diethyl ether (3×)
7. washwashed with brine (1×)
8. dry with materialdried over anhydrous sodium sulfate
9. concentrationconcentrated

ORD record

ord-afec1dc8e13e4cbea7f22f269e77608a

Source dataset

uspto-grants-2004_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06699904B2