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

HRID 1788892Notes

Reaction equation

HRID 1788892 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]>C.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 297MethaneSolventHCID 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 methan olic 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-61de906e5c764fd4a50908f805402d9d
Source dataset
uspto-grants-1987_08
Patent number
US04686213

Reaction notes

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