تفاعل #328820

معادلة التفاعل

sodium borohydride

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

N-methylmorpholine

isobutyl chloroformate

→

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

المذيبات

water

tetrahydrofuran

ظروف التفاعل

المعالجة

1. 1
   ترشيحThe resulting precipitate was filtered off
2. 2
   غسيلthe filter cake was washed with tetrahydrofuran (1 mL)
3. 3
   workup.STIRRINGThe resulting mixture was stirred for 1 h.
4. 4
   أخرىquenched with sodium bicarbonate aqueous solution
5. 5
   استخلاصThe mixture was extracted with ethyl acetate (55 mL)
6. 6
   غسيلThe organic layer was washed with brine (30 mL)
7. 7
   تجفيفdried over sodium sulfate
8. 8
   تركيزThe resulting solution was concentrated in vacuo
9. 9
   أخرىThe crude product (2.79 g) was used for the next step without purification

الإجراء التجريبي

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.

المصدر