Reaktion #325654

Reaktionsgleichung

1-Boc-azetidine-3-carboxylic acid

Et3N

Isopropyl chloroformate

→

compound

1-Boc-3-Hydroxymethyl-azetidine

Lösungsmittel

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigeforming a white precipitate almost immediately
2. 2
   Filtrationthe precipitate was filtered out
3. 3
   TemperaturThe filtrate was cooled to 0° C. again
4. 4
   workup.ADDITIONaqueous NaBH4 solution (900 mg, 5 ml) was added via pipette
5. 5
   workup.STIRRINGstirred for 1 h
6. 6
   SonstigeThe reaction was quenched with NaHCO3 solution (50 mL)
7. 7
   Extraktionthe product was extracted with EtOAc (200 mL)
8. 8
   WaschenThe organic phase was washed with brine (50 mL)
9. 9
   Trocknendried over Na2SO4
10. 10
    Einengenconcentrated in vacuo
11. 11
    workup.DISSOLUTIONThe residue was dissolved in EtOAc
12. 12
    EinengenConcentrating the filtrate in vacuo

Vorschrift

A solution of 1-Boc-azetidine-3-carboxylic acid (1.6 g) and Et3N (2 ml) in anhydrous THF (60 ml) was cooled to 0° C. Isopropyl chloroformate (1.3 g) was added via a syringe slowly; forming a white precipitate almost immediately. The reaction was stirred for 1 h at 0° C. and the precipitate was filtered out. The filtrate was cooled to 0° C. again and aqueous NaBH4 solution (900 mg, 5 ml) was added via pipette and stirred for 1 h. The reaction was quenched with NaHCO3 solution (50 mL) and the product was extracted with EtOAc (200 mL). The organic phase was washed with brine (50 mL), dried over Na2SO4 and concentrated in vacuo. The residue was dissolved in EtOAc and passed through a short silica gel pad. Concentrating the filtrate in vacuo provided the compound as a light yellow oil.

Quelle