3-Pyridinecarboxaldehyde → 2-Allyl-1-(3-pyridyl)-1,3-propanediol

온도

5 °C

A 1M solution of dibutylboron triflate in dichloromethane (32.7 ml) was added to a solution of A (6.28 g) in dry dichloromethane (110 ml), cooled to 5° C. under argon, followed by diisopropylethylamine (6.25 ml). The reaction mixture was stirred at 5° C. for 30 minutes and then cooled to -78° C. 3-Pyridinecarboxaldehyde (3.1 ml) was added dropwise. The mixture was stirred for 30 minutes at -78° C., and then allowed to warm to -50° C. over 30 minutes. The cooling bath was removed and the reaction mixture was stirred at room temperature for 2 hours. The mixture was then cooled to 5° C. and hydrogen peroxide (11.5 ml, 30% w/v aqueous solution) was added. The mixture was stirred for 30 minutes and then poured into water (50 ml) and extracted with dichloromethane (3×100 ml). The combined extracts were dried (MgSO4) and evaporated. The residue was purified by flash column chromatography, eluting with ethyl acetate/hexane (1:1 v/v, gradually increasing to 100% ethyl acetate), to give (4S)-(3-[(2S)-2-[(1S-1-hydroxy-1-(3-pyridyl)methyl]pent-4-enoyl)-4-isopropyloxazolidin-2-one (B), as a solid, m.p. 112°-113° C. (after recrystallisation from toluene); 25 [α]D =+136.0 (EtOH, c 0.311);

1. temperaturecooled to -78° C
2. stirringThe mixture was stirred for 30 minutes at -78° C.
3. temperatureto warm to -50° C. over 30 minutes
4. customThe cooling bath was removed
5. stirringthe reaction mixture was stirred at room temperature for 2 hours
6. temperatureThe mixture was then cooled to 5° C.
7. additionhydrogen peroxide (11.5 ml, 30% w/v aqueous solution) was added
8. stirringThe mixture was stirred for 30 minutes
9. additionpoured into water (50 ml)
10. extractionextracted with dichloromethane (3×100 ml)
11. dry with materialThe combined extracts were dried (MgSO4)
12. customevaporated
13. customThe residue was purified by flash column chromatography
14. washeluting with ethyl acetate/hexane (1:1 v/v
15. temperaturegradually increasing to 100% ethyl acetate),

ORD 기록

ord-dac36410a2dc41698d1739348f93e19e

출처 데이터셋

uspto-grants-1992_11

DOI

10.6084/m9.figshare.5104873.v1

특허 번호

US05166213