1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → 3-(2-Phenyl-piperidine-1-carbonyl)-piperidine-1-carboxlic acid tert.-butyl ester

To a solution of 2 g of 1-(tert-butoxycarbonyl)-3-piperidinecarboxylic acid (commercially available) (8.72 mmol) in 15 mL of DMF: DCM (3:1) was added 1.39 g 2-phenylpiperidine (commercially available) (8.72 mmol) and 3.04 mL DIPEA (17.4 mmol). The mixture was stirred at room temperature for 10 minutes. 2.5 g EDCI (13.1 mmol) and 2.04 g HOBT (13.1 mmol) was added. The mixture was stirred for 6 h at room temperature, diluted with brine (50 mL) and extracted with ethyl acetate (2×40 mL). The combined organic layers were dried over sodium sulfate, filtered and evaporated at reduced pressure to obtain the crude product, which was further purified by column chromatography on silica eluting with 30-35% ethyl acetate in hexane to yield 1 g (31%) of the title compound. (MH+) 372.18.

1. stirringThe mixture was stirred for 6 h at room temperature
2. extractionextracted with ethyl acetate (2×40 mL)
3. dry with materialThe combined organic layers were dried over sodium sulfate
4. filtrationfiltered
5. customevaporated at reduced pressure
6. customto obtain the crude product, which
7. customwas further purified by column chromatography on silica eluting with 30-35% ethyl acetate in hexane

ORDレコード

ord-b663db6a751e4092b02db1302cc23275

出典データセット

uspto-grants-2012_06

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US08202888B2