Cyclopentanol → Cyclopentyl 1-(6-chloro-2,3,4,9-tetrahydro-1H-beta-carbolin-1-yl)cyclobutanecarboxylate Hydrochloride

HRID 1700365Notes

Reaction equation

HRID 1700365 reaction equation
Cl.[Cl:2][C:3]1[CH:4]=[C:5]2[C:13](=[CH:14][CH:15]=1)[NH:12][C:11]1[CH:10]([C:16]3([C:20]([O:22][CH2:23][CH3:24])=[O:21])[CH2:19][CH2:18][CH2:17]3)[NH:9][CH2:8][CH2:7][C:6]2=1.[CH:25]1(O)[CH2:29]CC[CH2:26]1>O.CC(C)[O-].CC(C)[O-].CC(C)[O-].CC(C)[O-].[Ti+4]>[ClH:2].[Cl:2][C:3]1[CH:4]=[C:5]2[C:13](=[CH:14][CH:15]=1)[NH:12][C:11]1[CH:10]([C:16]3([C:20]([O:22][CH:23]4[CH2:29][CH2:25][CH2:26][CH2:24]4)=[O:21])[CH2:17][CH2:18][CH2:19]3)[NH:9][CH2:8][CH2:7][C:6]2=1

Participants

5

Reactant 2

HCID 7298CyclopentanolHCID 18317933Ethyl 1-(6-chloro-2,3,4,9-tetrahydro-1H-beta-carbolin-1-yl)cyclobutanecarboxylate Hydrochloride

Product 1

HCID 18317862Cyclopentyl 1-(6-chloro-2,3,4,9-tetrahydro-1H-beta-carbolin-1-yl)cyclobutanecarboxylate Hydrochloride

Reagents, catalysts & solvents 2

HCID 11026Titanium isopropoxideCatalystHCID 962WaterSolvent

Procedure

4.0 g of the compound of Example 1 are heated at the reflux of 80 ml of cyclopentanol in the presence of 1 ml of titanium tetraisopropoxide. After reaction for 24 hours, the reaction mixture is diluted with water and then filtered. After extraction with dichloromethane, drying and evaporation under reduced pressure, crystallisation of the residue from an ethanol-diethyl ether-hydrogen chloride mixture enables the expected product to be isolated.

Workup

  1. customAfter reaction for 24 hours
  2. filtrationfiltered
  3. extractionAfter extraction with dichloromethane
  4. customdrying
  5. customevaporation
  6. customunder reduced pressure, crystallisation of the residue from an ethanol-diethyl ether-hydrogen chloride mixture
  7. customto be isolated

Sources & evidence

ORD record
ord-e4421ef6078f48b99198835e66621569
Source dataset
uspto-grants-2002_02
Patent number
US06350757B1

Reaction notes

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