Hexamethyldisilazane → HCID 178483657, compound

Participants

Reaction Conditions

Reaction Steps

1.55 g (7.00 mmol) of trans-4-(2-methylamino-ethyl)-cyclohexanecarboxylic acid·HCl were mixed with 18.4 mL (12.56 mmol, 1.8 eq) of hexamethyldisilazane and heated under reflux to 145° C. for 2.5 h. The solution was evaporated, the residue was suspended in THF and treated with 1.07 g (7.70 mmol, 1.1 eq) of 4-chlorophenylchloroformate at 0° C. and the solution was stirred at RT overnight. 10 mL of water was added at RT followed by 10 mL of 1M NaOH. Stirring was continued for 1 h at RT. The organic solvent was evaporated and the residue partitioned between n-hexane (×3)/H2O. The water phase was acidified with 1M HCl and extracted with EtOAc (3×). The organic phase was dried over Na2SO4 and evaporated to yield 1.92 g (81%) of trans-4-{2-[(4-chloro-phenoxycarbonyl)-methyl-amino]-ethyl}-cyclohexanecarboxylic acid, MS: 338 (M−H−, 1Cl).

Provenance & Evidence