Hydrochloric Acid → methyl 3-benzyl-1,2,3,3a,4,5-hexahydro-4-(3-hydroxypropyl)-7H-pyrrolo(2,3-d)carbazole-6-carboxylate

HRID 330603Notes

Reaction equation

HRID 330603 reaction equation
[CH2:1]([N:8]1[CH2:21][CH2:20][C:19]2[C:18]3[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=3[NH:12][C:11]=2[CH:10]([C:22]([O:24][CH3:25])=[O:23])[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH:26][CH:27]1[CH2:32][CH2:31][CH2:30][CH2:29]O1.Cl.[OH-].[NH4+]>Cl.CO.O.CCOCC.C1(C)C=CC=CC=1>[CH2:1]([N:8]1[CH:9]2[CH:30]([CH2:31][CH2:32][CH2:27][OH:26])[CH2:29][C:10]([C:22]([O:24][CH3:25])=[O:23])=[C:11]3[NH:12][C:13]4[CH:14]=[CH:15][CH:16]=[CH:17][C:18]=4[C:19]23[CH2:20][CH2:21]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

10

Reactant 4

HCID 313Hydrochloric AcidHCID 14923Ammonium HydroxideHCID 1365052-HydroxytetrahydropyranHCID 11024114Azepino[4,5-B]indole-5-carboxylic acid,1,2,3,4,5,6-hexahydro-3-(phenylmethyl)-,methyl ester

Product 1

HCID 13856926methyl 3-benzyl-1,2,3,3a,4,5-hexahydro-4-(3-hydroxypropyl)-7H-pyrrolo(2,3-d)carbazole-6-carboxylateYield 100%

Reagents, catalysts & solvents 5

HCID 313Hydrochloric AcidCatalystHCID 887MethanolSolventHCID 962WaterSolventHCID 1140TolueneSolventHCID 3283Diethyl EtherSolvent

Conditions

Temperature
110 °C

Procedure

A mixture of methyl 3-benzyl-1,2,3,4,5,6-hexahydroazepino (4,5-b) indole-5-carboxylate (1.336 g, 4.0 mmol), 2-hydroxytetrahydropyran (0.980 g, 8.2 mmol), toluene (30 mL) and ether saturated with HCl gas (10 drops) was heated under a nitrogen atmosphere at 110° C. for 5 h. The reaction mixture was cooled, diluted with 15 mL of methanol and acidified with conc. hydrochloric acid. The reaction mixture was stirred for 12 h at 20° C., poured into 50 mL of water and made strongly basic with ammonium hydroxide. The toluene layer was separated and the aqueous portion extracted three times with 25 mL of dichloromethane. The combined organic solutions were washed three times with 25 mL of saturated brine, dried over sodium sulfate and concentrated at 50° C. under vacuum to provide 1.67 g (100%) of methyl 3-benzyl-1,2,3,3a,4,5-hexahydro-4-(3-hydroxypropyl)-7H-pyrrolo(2,3-d)carbazole-6-carboxylate, identical in spectroscopic properties and TLC Rf value to the product obtained in Example 1.

Workup

  1. temperatureThe reaction mixture was cooled
  2. customThe toluene layer was separated
  3. extractionthe aqueous portion extracted three times with 25 mL of dichloromethane
  4. washThe combined organic solutions were washed three times with 25 mL of saturated brine
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated at 50° C. under vacuum

Sources & evidence

ORD record
ord-c3a7d585fea84d66b86c89fb52108ef3
Source dataset
uspto-grants-1990_01
Patent number
US04897477

Reaction notes

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