反応 #1070243

反応方程式

1,4,5,6,7,8-hexahydro-pyrrolo[3,2-b]azepine

(S)-2-chlorocarbonyl-pyrrolidine-1-carboxylic acid tert-butyl ester

→

(S)-2-(5,6,7,8-tetrahydro-1H-pyrrolo[3,2-b]azepine-4-carbonyl)-pyrrolidine-1-carboxylic-acid tert-butyl ester

溶媒

DCM

反応条件

後処理

1. 1
   洗浄washed with NaHCO3, brine
2. 2
   その他dried
3. 3
   濃縮concentrated
4. 4
   その他The residue was purified on a silica gel column

実験手順

To a solution of(S)-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester (664 mg) in DCM (10 mL) at 0° C. was added oxalyl chloride (4.7 mmol), followed by one drop of DMF. After stirring at rt for 2 hours, the solvent was concentrated to give S) 2-chlorocarbonyl-pyrrolidine-1-carboxylic acid tert-butyl ester. To a solution of 1,4,5,6,7,8-hexahydro-pyrrolo[3,2-b]azepine (350 mg, 2.6 mmol) was added TEA (362 μL) and (S)-2-chlorocarbonyl-pyrrolidine-1-carboxylic acid tert-butyl ester (dissolved in 10 mL of DCM). After stirring at rt for overnight, the reaction was diluted with DCM, washed with NaHCO3, brine, dried and concentrated. The residue was purified on a silica gel column to give 410 mg of (S)-2-(5,6,7,8-tetrahydro-1H-pyrrolo[3,2-b]azepine-4-carbonyl)-pyrrolidine-1-carboxylic-acid tert-butyl ester as a light brown liquid.

出典