Реакция #69295

Уравнение реакции

1-[(benzyloxy)carbonyl]pyrrolidine-3-carboxylic acid

borane

HCl

→

Benzyl 3-(hydroxymethyl)pyrrolidine-1-carboxylate

Растворители

THF

THF

Условия реакции

Обработка

1. 1
   ТемператураThe mixture was cooled to 0° C.
2. 2
   workup.ADDITIONAfter the addition
3. 3
   Экстракцияthe mixture was extracted with DCM
4. 4
   Промывкаthe extract was washed sequentially with saturated NaHCO3 solution and brine
5. 5
   Сушкаdried over sodium sulfate
6. 6
   Фильтрацияfiltered
7. 7
   Другоеthe solvent was removed in vacuo
8. 8
   ДругоеThe product was used without further purification in the subsequent oxidation step

Методика

To a solution of 1-[(benzyloxy)carbonyl]pyrrolidine-3-carboxylic acid (1.0 g, 4.0 mmol) in THF (37 mL) at 0° C. was added dropwise a solution of 1.0 M borane in THF (16.4 mL). The reaction was allowed to warm to room temperature and stir for 16 hours. The mixture was cooled to 0° C. and 10% HCl (50 mL) was added. After the addition, the mixture was extracted with DCM, and the extract was washed sequentially with saturated NaHCO3 solution and brine, then dried over sodium sulfate, filtered and the solvent was removed in vacuo. The product was used without further purification in the subsequent oxidation step.

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