Reaction #60350

Reaction equation

(6-formyl-chroman-4-yl)-carbamic acid tert-butyl ester

piperidine

→

(6-piperidin-1-ylmethyl-chroman-4-yl)-carbamic acid tert-butyl ester

Conditions

Procedure

The reductive amination procedure in Example 1, Step H was used to react (6-formyl-chroman-4-yl)-carbamic acid tert-butyl ester (Step E) with piperidine to provide (6-piperidin-1-ylmethyl-chroman-4-yl)-carbamic acid tert-butyl ester. The Boc group was deprotected with TFA in CH2Cl2 to provide the amine salt. The coupling procedure described in the preparation of Example 1, Step F with 3-(naphthalen-2-yl-sulfonylamino)-3-phenylpropionic acid was used to provide the title compound as a mixture of diastereomers (ca. 1:1 by 1H NMR) isolated as the HCl salt. MS (ESI) 584 (M+H)+.

Source