Hydrochloric Acid → HCID 22473217, compound

Temperature

-78 °C

BuLi (6.87 ml of a 1.6 M solution in hexanes, 11.0 mmol) was added dropwise over 2 min to a stirred solution of dimethyl(2-[1,2,4]triazol-1-ylethyl)amine (1.4 g, 10 mmol) in THF (50 ml) at −78° C. under nitrogen. The resulting mixture was stirred at −78° C. for 15 min, then warmed to −40° C. and re-cooled to −78° C. DMF (2.31 ml, 30 mmol) was added and the reaction mixture warmed to room temperature and stirred for 15 min. MeOH was added followed by NaBH4 (567 mg, 15 mmol) and the reaction mixture stirred for 30 min. H2O (10 ml) was added followed by 1N HCl (50 ml). The reaction was left to stand overnight. The solvent was removed under reduced pressure and the aqueous extracted with CH2Cl2 (5×75 ml). The combined organic extracts were washed with brine (25 ml), dried (MgSO4) and concentrated under reduced pressure. The crude residue was azeotroped with xylene (2×100 ml) to yield the alcohol (1.24 g, 73%).

1. temperaturewarmed to −40° C.
2. temperaturere-cooled to −78° C
3. temperaturethe reaction mixture warmed to room temperature
4. stirringstirred for 15 min
5. stirringthe reaction mixture stirred for 30 min
6. waitThe reaction was left
7. waitto stand overnight
8. customThe solvent was removed under reduced pressure
9. extractionthe aqueous extracted with CH2Cl2 (5×75 ml)
10. washThe combined organic extracts were washed with brine (25 ml)
11. dry with materialdried (MgSO4)
12. concentrationconcentrated under reduced pressure
13. customThe crude residue was azeotroped with xylene (2×100 ml)

ORD record

ord-39aab653f5ad44b992d1bd84d99fd80a

Source dataset

uspto-grants-2005_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06900209B2