Pyrrolidine → HCID 22907290, compound

HRID 1379713Notes

Reaction equation

HRID 1379713 reaction equation
Cl.C([CH:4]1[C:8]([CH3:10])([CH3:9])[C:7]2[CH:11]=[C:12]([C:19](=[NH:21])O)[CH:13]=[C:14]([C:15]([CH3:18])([CH3:17])[CH3:16])[C:6]=2[O:5]1)C.[NH:22]1[CH2:26][CH2:25][CH2:24][CH2:23]1.CO.C(Cl)(Cl)[Cl:30]>O1CCOCC1>[ClH:30].[C:15]([C:14]1[C:6]2[O:5][CH2:4][C:8]([CH3:10])([CH3:9])[C:7]=2[CH:11]=[C:12]([C:19](=[NH:21])[N:22]2[CH2:26][CH2:25][CH2:24][CH2:23]2)[CH:13]=1)([CH3:18])([CH3:16])[CH3:17]

Participants

5

Reactant 3

HCID 31268PyrrolidineHCID 21584188Chloroform methanolHCID 178438097HCID 178438097, compound

Product 1

HCID 22907290HCID 22907290, compoundYield 54.2%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a solution of ethyl 7-tert-butyl-2,3-dihydro-3,3-dimethylbenzofuran-5-carboximidic acid hydrochloride (400 mg, 1.29 mmol) in dioxane (10 mL) is added excess pyrrolidine (0.6 mL). A color change from red to yellow is observed during the addition, and a precipitate forms. The reaction is also monitored by TLC (10% MeOH/CHCl3). After 3 h, the yellow precipitate is collected by filtration and purified by preparative TLC (10% MeOH/CHCl3) to give the desired product as a white powder (210 mg, 54.2%), mp=255°-256° C.

Workup

  1. additionA color change from red to yellow is observed during the addition
  2. filtrationthe yellow precipitate is collected by filtration
  3. custompurified by preparative TLC (10% MeOH/CHCl3)

Sources & evidence

ORD record
ord-9c7e101cd8e64f75b227e90ffad9419a
Source dataset
uspto-grants-1997_09
Patent number
US05672620

Reaction notes

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