Diketene → N-(2-bornyl)-acetylacetamide

HRID 426554노트

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HRID 426554 반응식
[CH2:1]=[C:2]1[O:6][C:4](=[O:5])[CH2:3]1.[C:7]12([CH3:17])[C:13]([CH3:15])([CH3:14])[CH:10]([CH2:11][CH2:12]1)[CH2:9][CH:8]2[NH2:16]>C(OC(C)C)(C)C>[C:7]12([CH3:17])[C:13]([CH3:14])([CH3:15])[CH:10]([CH2:11][CH2:12]1)[CH2:9][CH:8]2[NH:16][C:4](=[O:5])[CH2:3][C:2](=[O:6])[CH3:1]

참가 물질

4

반응물 2

HCID 12661DiketeneHCID 32526(1R,2S,4R)-Born-2-ylamine

생성물 1

HCID 18073029N-(2-bornyl)-acetylacetamide수율 83.9%

시약·촉매·용매 1

HCID 7914Diisopropyl Ether용매

반응 조건

온도
20 °C

실험 절차

16.8 g of diketene were added with stirring to a mixture of 30 g of 2-bornylamine and 200 ml of isopropyl ether and after stirring for 4 hours at 20° C., the mixture was evaporated to dryness under reduced pressure. The residue was chromatographed over silica gel and elution with a 9-1 methylene chloride-acetone mixture gave 39 g of N-(2-bornyl)-acetylacetamide. 30 g of the latter product and 1 g of p-toluene sulfonic acid were added to a mixture of 20 g of methyl orthoformate and 30 ml of methanol and the mixture stood at 20° C. for 16 hours. 2 ml of quinoline were added thereto and the mixture was evaporated to dryness under reduced pressure. The residue was added to toluene and the mixture was heated at 145° C. for 3 hours while distilling a toluene-methanol azeotrope. The mixture was evaporated to dryness under reduced pressure and the residue was chromatographed over silica gel. The product was eluted with an 8-2 methylene chloride-acetone mixture and was crystallized from isopropyl ether to obtain 19 g of N-(2'-bornyl)-3-methoxy-crotonamide melting at 149° C. The RMN spectra showed it was the E somer.

후처리

  1. customthe mixture was evaporated to dryness under reduced pressure
  2. customThe residue was chromatographed over silica gel and elution with a 9-1 methylene chloride-acetone mixture

출처 및 근거

ORD 기록
ord-ed8083d187034f8cb39439ab6c6f68ce
출처 데이터셋
uspto-grants-1979_10
특허 번호
US04170465

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