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Step 9b. (2S,4S)-1-BOC-4-amino-2-methylpyrrolidine (35) To a 1.95 g (6.71 mmol) sample of the compound from step 9a dissolved in 40 mL of absolute ethanol, stirred under nitrogen, was added 0.5 g of 10% Pd/C and 2.06 g (32.7 mmol) of ammonium formate. The temperature was raised to 60 C., and the reaction was stirred for 1 hour. The catalyst was filtered off, and the filtrate was concentrated under vacuum to afford after drying 1.38 g (100% yield) of the title compound as a viscous oil.
23
[ 1235406-85-5 ]
[ 152673-32-0 ]
tert-butyl (2S,4S)-4-((4-(N-(tert-butoxycarbonyl)-N-(thiazol-4-yl)sulfamoyl)-2-chloro-5-fluorophenyl)amino)-2-methylpyrrolidine-1-carboxylate[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
55%
With triethylamine; In dimethyl sulfoxide; at 20.0℃; for 16.0h;
EXAMPLE 231 Synthesis of 4-(((3S,5S)-1-benzyl-5-methylpyrrolidin-3-yl)(methyl)amino)-5-chloro-2- fluoro-Ay-(thiazol-4-yl)benzenesulfonamide formate Step 1. Preparation of te/f-butyl (2S,4S)-4-((4-(Ay-(te/f-butoxycarbonyl)-Ay-(thiazol-4- yl)sulfamoyl)-2-chloro-5-fluorophenyl)amino)-2-methylpyrrolidine-1-carboxylate To a solution of terf-butyl ((5-chloro-2,4-difluorophenyl)sulfonyl)(thiazol-4- yl)carbamate (1.71 g, 4.16 mmol) in anhydrous dimethyl sulfoxide (8 mL) was added te/f-butyl (2S,4S)-4-amino-2-methylpyrrolidine-1-carboxylate (1.00 g, 4.99 mmol) followed by triethylamine (0.70 mL, 4.99 mmol). The resulting solution was stirred at ambient temperature for 16 h. The crude reaction mixture was purified by column chromatography, eluting with 0 to 100% of ethyl acetate in heptane, to provide the title compound as a colorless solid (1.62 g, 55% yield).
(2S,4S)-4-(3,5-dimethylpyridin-2-ylamino)-2-methylpyrrolidine-1-carboxylic acid tert-butyl ester[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
192 mg
With N-ethyl-N,N-diisopropylamine; bromo-tris(1-pyrrolidinyl)phosphonium hexafluorophosphate; In dichloromethane; at 20.0℃;
<strong>[152673-32-0](2S,4S)-4-amino-2-methylpyrrolidine-1-carboxylic acid tert-butyl ester</strong> (280 mg) was dissolved in dichloromethane (6 mL),diisopropylethylamine (0.913 mL),3,5-dimethylpyridine-N-oxide (172 mg) and bromotris(pyrrolidino)phosphonium hexafluorophosphate (847 mg) were added, and the mixture was stirred at room temperature overnight. 3,5-Dimethylpyridine-N-oxide (86 mg) and bromotris(pyrrolidino)phosphonium hexafluorophosphate (325 mg) were added, and the mixture was stirred at room temperature for 3 hr. The reaction mixture was concentrated under reduced pressure,and the obtained residue was purified by NH column chromatography (hexane:ethyl acetate)to give (2S,4S)-4-(3,5-dimethylpyridin-2-ylamino)-2-methylpyrrolidine-1-carboxylic acid tert-butyl ester (192 mg).
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