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

HRID 2270453ノート

反応式

HRID 2270453 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

実験手順

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%.

後処理

  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

出典と根拠

ORDレコード
ord-5901b5815f864641bba64ca3b700173c
出典データセット
uspto-grants-2001_12
特許番号
US06331638B1

反応ノート

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