Dicyclohexylcarbodiimide → 4,4-Dimethyl-7-(4-p-Fluorophenyl-1-Methylbutyl)-9-[4-(Pyrrolidino)-Butyryloxy]-1,2,3,4-Tetrahydrocyclopenta[c] [1]Benzopyran Hydrochloride

HRID 2071976Notes

Reaction equation

HRID 2071976 reaction equation
[CH3:1][C:2]1([CH3:28])[C:7]2[CH2:8][CH2:9][CH2:10][C:6]=2[C:5]2[C:11]([OH:27])=[CH:12][C:13]([CH:15]([CH3:26])[CH2:16][CH2:17][CH2:18][C:19]3[CH:24]=[CH:23][C:22]([F:25])=[CH:21][CH:20]=3)=[CH:14][C:4]=2[O:3]1.[ClH:29].[N:30]1([CH2:35][CH2:36][CH2:37][C:38](O)=[O:39])[CH2:34][CH2:33][CH2:32][CH2:31]1.C1(N=C=NC2CCCCC2)CCCCC1>C(Cl)Cl>[ClH:29].[CH3:28][C:2]1([CH3:1])[C:7]2[CH2:8][CH2:9][CH2:10][C:6]=2[C:5]2[C:11]([O:27][C:38](=[O:39])[CH2:37][CH2:36][CH2:35][N:30]3[CH2:34][CH2:33][CH2:32][CH2:31]3)=[CH:12][C:13]([CH:15]([CH3:26])[CH2:16][CH2:17][CH2:18][C:19]3[CH:24]=[CH:23][C:22]([F:25])=[CH:21][CH:20]=3)=[CH:14][C:4]=2[O:3]1

Participants

5

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 148556824-(Pyrrolidin-1-yl)butanoic acid hydrochlorideHCID 214097494,4-Dimethyl-9-hydroxy-7-(4-p-fluorophenyl-1-methylbutyl)-1,2,3,4-tetrahydrocyclopenta [c] [1]benzopyran

Product 1

HCID 681215564,4-Dimethyl-7-(4-p-Fluorophenyl-1-Methylbutyl)-9-[4-(Pyrrolidino)-Butyryloxy]-1,2,3,4-Tetrahydrocyclopenta[c] [1]Benzopyran Hydrochloride

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3.55 g. (9.37 mmoles) of 4,4-dimethyl-9-hydroxy-7-(4-p-fluorophenyl-1-methylbutyl)-1,2,3,4-tetrahydrocyclopenta [c] [1]benzopyran are combined with 1.82 g. (9.37 mmoles) of γ-pyrrolidinobutyric acid hydrochloride and 2.06 g. (10.0 mmoles) of dicyclohexylcarbodiimide in 150 ml. of methylene chloride and stirred at room temperature for 21/2 hours. The insoluble by-product of dicyclohexylurea is removed by filtration and the filtrate is evaporated to give a residue which crystallized upon standing. The material is triturated with ether and filtered. Recrystallization from benzene-ether gives the product as colorless crystals.

Workup

  1. customThe insoluble by-product of dicyclohexylurea is removed by filtration
  2. customthe filtrate is evaporated
  3. customto give a residue which
  4. customcrystallized
  5. customThe material is triturated with ether
  6. filtrationfiltered
  7. customRecrystallization from benzene-ether

Sources & evidence

ORD record
ord-9f2349e37ab54ce39abfec7f15be4f14
Source dataset
uspto-grants-1977_09
Patent number
US04049653

Reaction notes

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