Reaktion #69295

Reaktionsgleichung

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

borane

HCl

→

Benzyl 3-(hydroxymethyl)pyrrolidine-1-carboxylate

Lösungsmittel

THF

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturThe mixture was cooled to 0° C.
2. 2
   workup.ADDITIONAfter the addition
3. 3
   Extraktionthe mixture was extracted with DCM
4. 4
   Waschenthe extract was washed sequentially with saturated NaHCO3 solution and brine
5. 5
   Trocknendried over sodium sulfate
6. 6
   Filtrationfiltered
7. 7
   Sonstigethe solvent was removed in vacuo
8. 8
   SonstigeThe product was used without further purification in the subsequent oxidation step

Vorschrift

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.

Quelle