Реакция #169944

Уравнение реакции

Sodium borohydride

4-benzylmorpholine-2-carboxylic acid

triethylamine

citric acid

ethyl carbonochloridate

→

title compound

Выход 64.0%

(4-benzylmorpholin-2-yl)methanol

Выход 64.0%

Растворители

methanol

THF

Условия реакции

Обработка

1. 1
   Температураto warm to room temperature
2. 2
   Концентрированиеconcentrated under reduced pressure
3. 3
   workup.DISSOLUTIONThe residue was dissolved in EtOAc
4. 4
   Промывкаwashed with water, brine
5. 5
   Сушкаdried with MgSO4
6. 6
   ДругоеPurification of the residue
7. 7
   Промывкаby column chromatography (SiO2, eluted with EtOAc)

Методика

To a solution of 4-benzylmorpholine-2-carboxylic acid (5 g, 22.6 mmol) and triethylamine (3.35 mL, 24 mmol) in THF (100 mL) at −10° C. in a flask equipped with a condenser was added ethyl carbonochloridate (2.5 g, 23 mmol) dropwise and the mixture was stirred at −10° C. to −5° C. for 20 min. Sodium borohydride (2.27 g, 60 mmol) was added followed by methanol (25 mL) from the top of the condenser at such rate to maintain the temperature between 0-5° C. The reaction mixture was allowed to warm to room temperature, acidified to pH 5 with the addition of 10% aqueous citric acid, and concentrated under reduced pressure. The residue was dissolved in EtOAc, washed with water, brine, and dried with MgSO4. Purification of the residue by column chromatography (SiO2, eluted with EtOAc) afforded 3 g of the title compound. MS (DCI/NH3) m/z 208 (M+H)+.

Источник