Dichloromethane → (4-nitro-3-trifluoromethyl-phenyl)-(R)-pyrrolidin-3-yl-amine hydrochloride

Reaktionsgleichung

C(OC([N:8]1[CH2:12][CH2:11][C@@H:10]([NH:13][C:14]2[CH:19]=[CH:18][C:17]([N+:20]([O-:22])=[O:21])=[C:16]([C:23]([F:26])([F:25])[F:24])[CH:15]=2)[CH2:9]1)=O)(C)(C)C.FC(F)(F)C(O)=O.[Cl:34]CCl>>[ClH:34].[N+:20]([C:17]1[CH:18]=[CH:19][C:14]([NH:13][C@@H:10]2[CH2:11][CH2:12][NH:8][CH2:9]2)=[CH:15][C:16]=1[C:23]([F:26])([F:24])[F:25])([O-:22])=[O:21]

Komponenten

Edukt 3

HCID 6344Dichloromethane

HCID 6422Trifluoroacetic acid

HCID 58576068(R)-3-(4-nitro-3-trifluoromethyl-phenylamino)-pyrrolidine-1-carboxylic acid tert-butyl ester

Produkt 1

HCID 67995634(4-nitro-3-trifluoromethyl-phenyl)-(R)-pyrrolidin-3-yl-amine hydrochloride

Versuchsvorschrift

To solid (R)-3-(4-Nitro-3-trifluoromethyl-phenylamino)-pyrrolidine-1-carboxylic acid tert-butyl ester (1.12 g; 2.98 mmol, prepared in accordance with Example 164) is added a 3:2 mixture of dichloromethane and trifluoroacetic acid (5 mL) and the resulting solution is stirred at room temperature for 2 hours. All volatiles are then removed under high vacuum and the residue taken up in ethyl acetate. A 4 molar solution of hydrochloric acid in dioxane is then added and, after formation of an oily precipitate, all volatiles removed under high vacuum. The obtained residue is then taken up in methanol and treated with diethyl ether. This mixture is allowed to stand over night, concentrated under high vacuum and taken up in hot ethyl acetate. The solution is then allowed to stand at room temperature over night and the precipitate formed is collected and dried under high vacuum to afford the desired compound (1.07 g) which is used in the next step without further purification.