HCID 14146234, compound → Methyl 4-amino-1,8-diethyl-1,3,4,9-tetrahydropyrano[3,4-b]indole-1-acetate

HRID 1253285Notes

Reaction equation

HRID 1253285 reaction equation
[CH3:1][O:2][C:3](=[O:25])[CH2:4][C:5]1([CH2:23][CH3:24])[C:10]2[NH:11][C:12]3[C:17]([C:9]=2[CH:8]([NH:20]C=O)[CH2:7][O:6]1)=[CH:16][CH:15]=[CH:14][C:13]=3[CH2:18][CH3:19]>Cl.CO>[CH3:1][O:2][C:3](=[O:25])[CH2:4][C:5]1([CH2:23][CH3:24])[C:10]2[NH:11][C:12]3[C:17]([C:9]=2[CH:8]([NH2:20])[CH2:7][O:6]1)=[CH:16][CH:15]=[CH:14][C:13]=3[CH2:18][CH3:19]

Participants

4

Reactant 1

HCID 14146234HCID 14146234, compound

Product 1

HCID 4196618Methyl 4-amino-1,8-diethyl-1,3,4,9-tetrahydropyrano[3,4-b]indole-1-acetateYield 50%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 887MethanolSolvent

Procedure

1,8-Diethyl-4-formylamino-1,3,4,9-tetrahydropyrano[3,4-b]indole-1-acetic acid methyl ester 10 (5.5 g, 0.01 mol) in 1N methanolic HCl (4.2 mL) and methanol (18 mL) was stirred at 25° C. for 72 hours, then concentrated in vacuo, diluted with water and extracted with ethyl acetate. The aqueous phase was basified with concentrated NaHCO3 solution and extracted with ether to afford the product (1.58 g, 50%), m.p. 230° C. (dec.) after recrystallization from ether.

Workup

  1. concentrationconcentrated in vacuo
  2. additiondiluted with water
  3. extractionextracted with ethyl acetate
  4. extractionextracted with ether

Sources & evidence

ORD record
ord-1d653bf4e5f04314b39c0736df341f5b
Source dataset
uspto-grants-1988_05
Patent number
US04748252

Reaction notes

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