Hydrochloric Acid → Methyl 1,8-diethyl-1,3,4,9-tetrahydropyrano(3,4-b)indole-1-acetate

HRID 2270453노트

반응식

HRID 2270453 반응식
[CH3:1][CH2:2][C:3]1[C:8]2[NH:9][CH:10]=[C:11]([CH2:12][CH2:13][OH:14])[C:7]=2[CH:6]=[CH:5][CH:4]=1.Cl.O=[C:17]([CH2:23][CH3:24])[CH2:18][C:19]([O:21][CH3:22])=[O:20]>C1(C)C=CC=CC=1>[CH2:23]([C:17]1([CH2:18][C:19]([O:21][CH3:22])=[O:20])[C:10]2[NH:9][C:8]3[C:7]([C:11]=2[CH2:12][CH2:13][O:14]1)=[CH:6][CH:5]=[CH:4][C:3]=3[CH2:2][CH3:1])[CH3:24]

참가 물질

5

반응물 3

HCID 313Hydrochloric AcidHCID 121699Methyl 3-oxovalerateHCID 1982317-Ethyltryptophol

생성물 1

HCID 527310Methyl 1,8-diethyl-1,3,4,9-tetrahydropyrano(3,4-b)indole-1-acetate수율 84%

시약·촉매·용매 1

HCID 1140Toluene용매

실험 절차

To a solution of 7-ethyltryptophol (12.0 g) in a mixture of methanolic hydrogen chloride (10% w/v, 50.0 ml) and toluene (50 ml), methyl 3-oxopentanoate (9.1 g, 0.07 mole) was added in one lot, at 25° C. The reaction mixture was stirred at 25-30° c for 7 hours. The reaction mixture concentrated to about 20 ml under reduced pressure. Methanol (50 ml) was added to the concentrate and the solution was extracted with hexane (100 ml). Hexane was concentrated to about 20 ml and methanol (10 ml) was added. The product was filtered, washed with methanol and dried to afford the title compound (15.8 g, 84%), m.p. 128-130° C., purity: 97.8%.

후처리

  1. additionwas added in one lot, at 25° C
  2. concentrationThe reaction mixture concentrated to about 20 ml under reduced pressure
  3. additionMethanol (50 ml) was added to the
  4. concentrationconcentrate
  5. extractionthe solution was extracted with hexane (100 ml)
  6. concentrationHexane was concentrated to about 20 ml and methanol (10 ml)
  7. additionwas added
  8. filtrationThe product was filtered
  9. washwashed with methanol
  10. customdried

출처 및 근거

ORD 기록
ord-5901b5815f864641bba64ca3b700173c
출처 데이터셋
uspto-grants-2001_12
특허 번호
US06331638B1

반응 노트

불러오는 중…