Реакция #1485564

Уравнение реакции

(S)-tert-butyl (4-methyl-1-oxopentan-2-yl)carbamate

methyl magnesium bromide

→

tert-butyl ((3S)-2-hydroxy-5-methylhexan-3-yl)carbamate

Выход 71.5%

Растворители

diethyl ether

Условия реакции

Обработка

1. 1
   workup.STIRRINGstirred for an additional hour at RT
2. 2
   ДругоеThe reaction mixture was quenched with NH4Cl
3. 3
   ЭкстракцияThe reaction mixture was extracted with diethyl ether (3×100 mL)
4. 4
   ПромывкаThe combined organic layers were washed with brine
5. 5
   Сушкаdried over MgSO4
6. 6
   Концентрированиеconcentrated

Методика

A solution of (S)-tert-butyl (4-methyl-1-oxopentan-2-yl)carbamate (1.3 g, 6.04 mmol) in diethyl ether (50 mL) was cooled to −78° C. and treated with methyl magnesium bromide (1.4 M in diethyl ether) (8.63 mL, 12.08 mmol). The slurry was stirred at 0° C. for 1 h and then stirred for an additional hour at RT. The reaction mixture was quenched with NH4Cl. The reaction mixture was extracted with diethyl ether (3×100 mL). The combined organic layers were washed with brine, dried over MgSO4, and concentrated to afford the product, tert-butyl ((3S)-2-hydroxy-5-methylhexan-3-yl)carbamate (1 g, 4.32 mmol, 72% crude yield) as colorless oil. The material was carried on without further purification. 1H NMR (300 MHz, DMSO-d6): δ 0.78-0.93 (m, 6H), 0.98 (d, 3H), 1.11-1.41 (m, 2H), 1.42 (s, 9H), 1.45-1.64 (m, 1H), 3.30-3.63 (m, 2H), 4.37 (d, 1H), 6.19 (d, 1H).

Источник