Reaktion #328820

Reaktionsgleichung

sodium borohydride

1-(tert-butoxycarbonyl)azetidine-3-carboxylic acid

N-methylmorpholine

isobutyl chloroformate

→

tert-butyl 3-(hydroxymethyl)azetidine-1-carboxylate

Lösungsmittel

water

tetrahydrofuran

Reaktionsbedingungen

Aufarbeitung

1. 1
   FiltrationThe resulting precipitate was filtered off
2. 2
   Waschenthe filter cake was washed with tetrahydrofuran (1 mL)
3. 3
   workup.STIRRINGThe resulting mixture was stirred for 1 h.
4. 4
   Sonstigequenched with sodium bicarbonate aqueous solution
5. 5
   ExtraktionThe mixture was extracted with ethyl acetate (55 mL)
6. 6
   WaschenThe organic layer was washed with brine (30 mL)
7. 7
   Trocknendried over sodium sulfate
8. 8
   EinengenThe resulting solution was concentrated in vacuo
9. 9
   SonstigeThe crude product (2.79 g) was used for the next step without purification

Vorschrift

To a solution of 1-(tert-butoxycarbonyl)azetidine-3-carboxylic acid (3.00 g, 14.9 mmol) in tetrahydrofuran (15 mL) was added N-methylmorpholine (1.80 mL, 16.4 mmol) and isobutyl chloroformate (2.13 mL, 16.4 mmol) at 0° C. The mixture was stirred for 20 min. The resulting precipitate was filtered off and the filter cake was washed with tetrahydrofuran (1 mL). The filtrate was cooled to 0° C. and a solution of sodium borohydride (0.846 g, 22.4 mmol) in water (2 mL) was added. The resulting mixture was stirred for 1 h. and quenched with sodium bicarbonate aqueous solution. The mixture was extracted with ethyl acetate (55 mL). The organic layer was washed with brine (30 mL) and dried over sodium sulfate. The resulting solution was concentrated in vacuo. The crude product (2.79 g) was used for the next step without purification.

Quelle