تفاعل #584749

معادلة التفاعل

Methyl magnesium bromide

tert-butyl (1S)-2-[methoxy(methyl)amino]-1-methyl-2-oxoethylcarbamate

ammonium chloride

→

title compound

المردود 51.0%

tert-Butyl (1S)-1-methyl-2-oxopropylcarbamate

المردود 51.0%

المذيبات

tetrahydrofuran

ظروف التفاعل

المعالجة

1. 1
   استخلاصaqueous phase was extracted with diethyl ether (2×76 ml)
2. 2
   غسيلThe combined organic extracts were then washed with saturated aqueous ammonium chloride solution and brine
3. 3
   تجفيفThe organic phase was then dried (MgSO4)
4. 4
   ترشيحfiltered
5. 5
   تركيزconcentrated under reduced pressure
6. 6
   أخرىThe residue was purified by column chromatography on silica gel
7. 7
   غسيلeluting with a solvent gradient of dichloromethane:methanol (99:1 to 98:2)

الإجراء التجريبي

Methyl magnesium bromide (3.0M solution in diethyl ether, 4.3 ml, 12.9 mmol) was added to a stirred solution of tert-butyl (1S)-2-[methoxy(methyl)amino]-1-methyl-2-oxoethylcarbamate (Tetrahedron: Asymmetry 1996, 7, 985) (1 g, 4.3 mmol) in anhydrous tetrahydrofuran (20 ml) at −60° C. under a nitrogen atmosphere. The mixture was allowed to warm to 0° C. and to then room temperature and was stirred at room temperature for 1 hour. Aqueous saturated ammonium chloride was added and aqueous phase was extracted with diethyl ether (2×76 ml). The combined organic extracts were then washed with saturated aqueous ammonium chloride solution and brine. The organic phase was then dried (MgSO4), filtered, and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel, eluting with a solvent gradient of dichloromethane:methanol (99:1 to 98:2), to afford the title compound as a colorless solid, 412 mg, 51% yield.

المصدر