Tetrahydrofuran → HCID 59190365, compound

A 250-mL RBF equipped with a magnetic stirbar was charged with solid (S)—N-(1-(4-bromophenyl)ethyl)-4-oxo-4-phenylbutanamide (2.85 g, 7.9 mmol) and placed in an ice bath. To the stirred solid was added 1.0 M BH3 in THF (30 mL, 30 mmol). The ice bath was removed and the mixture was stirred at rt for 2.5 h. The mixture was poured into 5% aq HCl (100 mL) and concentrated under reduced pressure to remove the THF. The aqueous residue was basified to pH 14 by portionwise addition of NaOH pellets. The mixture was extracted with CH2Cl2 (2×100 mL). The combined CH2Cl2 extracts were dried over Na2SO4. Removal of the solvent afforded crude 4-((S)-1-(4-bromophenyl)ethylamino)-1-phenylbutan-1-ol (2.58 g, 94%) as an oil. LC-MS Method 1 tR=1.20 min, m/z=348, 350.

1. customA 250-mL RBF equipped with a magnetic stirbar
2. customplaced in an ice bath
3. additionTo the stirred solid was added 1.0 M
4. customThe ice bath was removed
5. additionThe mixture was poured into 5% aq HCl (100 mL)
6. concentrationconcentrated under reduced pressure
7. customto remove the THF
8. additionThe aqueous residue was basified to pH 14 by portionwise addition of NaOH pellets
9. extractionThe mixture was extracted with CH2Cl2 (2×100 mL)
10. dry with materialThe combined CH2Cl2 extracts were dried over Na2SO4
11. customRemoval of the solvent

ORD record

ord-5ccaa0c568384effbd651e221b1c0374

Source dataset

uspto-grants-2012_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08202857B2