N,N,N',N'-Tetramethylethylenediamine → Tert-butyl 2-{4-[(dimethylamino)methyl]phenyl}-2-hydroxyethyl(methyl)carbamate

To a solution of tert-butyl dimethylcarbamate (350 mg, 2.4 mmol) and tetramethylethylenediamine (511 mg, 4.4 mmol) in THF (anhydrous, 10 mL) was added sec-butyllithium (1.4 M in cyclohexane, 2.2 mL, 3.1 mmol) at −78° C. The mixture was stirred at that temperature for 1 hour before 4-[(dimethylamino)methyl]benzaldehyde (J.Heterocycl.Chem.; 26; 1989; 1325-1330)(280 mg, 1.7 mmol) was introduced. The reaction mixture was stirred for 2 hours, warmed to room temperature and stirred for 1 hour. Saturated ammonium chloride aqueous solution (10 mL) was added to quench the reaction after the reaction mixture was cooled to −78° C. The organic phase was separated and the aqueous phase was extracted with dichloromethane. The organic phases were combined, washed with brine and dried over sodium sulfate and concentrated. The residue was purified with a silica gel column to give the title compound (0.40 g) as a white solid.

1. additionwas introduced
2. stirringstirred for 1 hour
3. customto quench
4. customthe reaction after the reaction mixture
5. temperaturewas cooled to −78° C
6. customThe organic phase was separated
7. extractionthe aqueous phase was extracted with dichloromethane
8. washwashed with brine
9. dry with materialdried over sodium sulfate
10. concentrationconcentrated
11. customThe residue was purified with a silica gel column

ORD-Eintrag

ord-6511676a45de4e4a8f11cbf1be38cd8d

Quelldatensatz

uspto-grants-2005_02

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US06852731B2