Hydrochloric Acid → HCID 14146236, compound

HRID 1253286Notes

Reaction equation

HRID 1253286 reaction equation
[CH3:1][O:2][C:3](=[O:23])[CH2:4][C:5]1([CH2:21][CH3:22])[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].Cl.[O-:25][C:26]#[N:27].[K+]>C(O)C.O>[CH3:1][O:2][C:3](=[O:23])[CH2:4][C:5]1([CH2:21][CH3:22])[C:10]2[NH:11][C:12]3[C:17]([C:9]=2[CH:8]([NH:20][C:26]([NH2:27])=[O:25])[CH2:7][O:6]1)=[CH:16][CH:15]=[CH:14][C:13]=3[CH2:18][CH3:19]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 4196618Methyl 4-amino-1,8-diethyl-1,3,4,9-tetrahydropyrano[3,4-b]indole-1-acetateHCID 11378442Potassium cyanate

Product 1

HCID 14146236HCID 14146236, compoundYield 75%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a solution of 4-amino-1,8-diethyl-1,3,4,9-tetrahydro[3,4-b]indole-1-acetic acid methyl ester 12 (prepared in Example 1) (1.10 g, 3.48 mmol) in ethanol (20 mL), stirred at room temperature under nitrogen, was added aqueous 1N HCl (6.96 mL) followed by potassium cyanate (0.565 g, 6.96 mmol) dissolved in a little water. After 2 hours the ethanol was removed in vacuo and the residue was extracted with ethyl acetate. Drying (MgSO4) and flash chromatography (1% MeOH in EtOAc eluent) afforded the product (0.714 g, 75%) as a mixture of diastereomers which were separated by reverse phase chromatography (C18 silica gel; 30% acetonitrile in water). The less polar Isomer A (190 mg) had m.p. 179.5°-180.5° C. (methylene chloride-petroleum ether).

Workup

  1. customAfter 2 hours the ethanol was removed in vacuo
  2. extractionthe residue was extracted with ethyl acetate
  3. dry with materialDrying (MgSO4) and flash chromatography (1% MeOH in EtOAc eluent)

Sources & evidence

ORD record
ord-3fdb6c01302a451f85cbd74c0c521192
Source dataset
uspto-grants-1988_05
Patent number
US04748252

Reaction notes

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