4-Cyano-4-(toluene-4-sulfonyloxyMethyl)-piperidine-1-carboxylic acid tert-butyl ester synthesis
- Product Name:4-Cyano-4-(toluene-4-sulfonyloxyMethyl)-piperidine-1-carboxylic acid tert-butyl ester
- CAS Number:929302-00-1
- Molecular formula:C19H26N2O5S
- Molecular Weight:394.49
Yield:929302-00-1 68%
Reaction Conditions:
Stage #1: tert-butyl 4-cyano-4-(hydroxymethyl) piperidine-1-carboxylate;p-toluenesulfonyl chloridewith dmap;triethylamine in dichloromethane at 5 - 10;
Stage #2: with hydrogenchloride in dichloromethane;water; pH=5 - 6;
Steps:
Preparation of compound 3To a solution of compound 2 (6.3 g) in 60 mL of DCM were added Et3N (4 mL) and DMAP (0.2 g). The mixture was cooled to 5 °C - 10 °C and a solution of TsCl (5.5 g, 9 mmol) in 40 mL of DCM was added dropwise. After the addition, water was added to dissolve some dissoluble material. Then the mixture was adjusted to pH 5~6 with aq. HCl. The organic layer was separated, washed to pH 7 with water, dried over Na2SO4 and concentrated. The residue was purified by column to give the compound 3 (7 g, 68%).
References:
WO2007/30061,2007,A1 Location in patent:Page/Page column 92; 93
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