Dichloromethane → HCID 21195983, Verbindung

Temperatur

-45 °C

A stirred solution of 4-(t-butoxycarbonylamino)-2,2-dimethylbutan-1-ol (1.5 g, 6.90 mmol) in tetrahydrofuran (49 ml) at −45° C. was treated with potassium t-butoxide (1 M in tetrahydrofuran, 7.59 ml, 7.59 mmol). The anion was stirred for 30 minutes at −45° C., then cooled to −78° C. and treated with a tetrahydrofuran solution of 2-fluoro-5-bromobenzyl bromide (1.85 g, 6.90 mmol). The resulting yellow mixture was slowly warmed to ambient temperature and stirred for about 18 hours. The cloudy reaction mixture was diluted wtih methylene chloride and washed with 1 M potassium carbonate. The organic fraction was dried over sodium sulfate, filtered, and the solvents were removed in vacuo. The residue was further purified by preparative high performance liquid chromatography to yield 1.45 grams (52%) of the title intermediate as a colorless oil.

1. temperaturecooled to −78° C.
2. temperatureThe resulting yellow mixture was slowly warmed to ambient temperature
3. stirringstirred for about 18 hours
4. customThe cloudy reaction mixture
5. washwashed with 1 M potassium carbonate
6. dry with materialThe organic fraction was dried over sodium sulfate
7. filtrationfiltered
8. customthe solvents were removed in vacuo
9. customThe residue was further purified by preparative high performance liquid chromatography

ORD-Eintrag

ord-c9eb6c5f4d7243abafdf9287c56bcb47

Quelldatensatz

uspto-grants-2001_06

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US06245761B1