تفاعل #78130

معادلة التفاعل

sodium borohydride

Boc-isonipecotic acid

N-methylmorpholine

ethyl chloroformate

→

title compound

المردود 92.4%

1-Boc-piperidine-4-methanol

المردود 92.4%

المذيبات

tetrahydrofuran

ظروف التفاعل

المعالجة

1. 1
   workup.ADDITIONvia addition funnel
2. 2
   أخرىthen it was slowly quenched with methanol
3. 3
   أخرىThe solvent was removed in vacuo
4. 4
   workup.ADDITIONthe resulting residue was diluted with 10% aqueous acetic acid
5. 5
   أخرىpartitioned between ethyl acetate and water
6. 6
   أخرىThe aqueous layer was separated
7. 7
   استخلاصextracted with additional ethyl acetate (2×500 mL)
8. 8
   تجفيفThe combined organic extracts were dried with magnesium sulfate
9. 9
   ترشيحfiltered
10. 10
    تركيزconcentrated in vacuo to a solid residue which
11. 11
    أخرىwas chromatographed on silica gel
12. 12
    غسيلElution with ethyl acetate-hexanes (1:9 to 1:1)

الإجراء التجريبي

To a solution of Boc-isonipecotic acid (40 g, 0.17 mol) and N-methylmorpholine (19 mL, 0.17 mol) in tetrahydrofuran (900 mL) stirring at −10° C., ethyl chloroformate was slowly added (17 mL, 0.17 mol) via addition funnel. After 30 min, sodium borohydride was added (19.8 g, 0.5 mol) in one portion. The reaction mixture was stirred at −10° C. for 1 h; then it was slowly quenched with methanol. The solvent was removed in vacuo; the resulting residue was diluted with 10% aqueous acetic acid and partitioned between ethyl acetate and water. The aqueous layer was separated and extracted with additional ethyl acetate (2×500 mL). The combined organic extracts were dried with magnesium sulfate, filtered, and concentrated in vacuo to a solid residue which was chromatographed on silica gel. Elution with ethyl acetate-hexanes (1:9 to 1:1) provided the title compound (33.8 g, 90%) as a white solid.

المصدر