Hydrochloric Acid → Methyl 1,8-diethyl-1,3,4,9-tetrahydropyrano(3,4-b)indole-1-acetate
Reaction equation
[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]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
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%.
Workup
- additionwas added in one lot, at 25° C
- concentrationThe reaction mixture concentrated to about 20 ml under reduced pressure
- additionMethanol (50 ml) was added to the
- concentrationconcentrate
- extractionthe solution was extracted with hexane (100 ml)
- concentrationHexane was concentrated to about 20 ml and methanol (10 ml)
- additionwas added
- filtrationThe product was filtered
- washwashed with methanol
- customdried
Sources & evidence
- ORD record
- ord-5901b5815f864641bba64ca3b700173c
- Source dataset
- uspto-grants-2001_12
- Patent number
- US06331638B1
Reaction notes
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