1,2-Dichloroethane → 4-[(4-Cyclobutylmethoxy-1H-indole-2-carbonyl)-amino]-piperidine-1-carboxylic acid tert-butyl ester

Participants

Role	Name	HCID	Charge
Reactant	1,2-Dichloroethane	HCID 11	—
Reactant	Triethylamine	HCID 8471	—
Reactant	1-Hydroxybenzotriazole	HCID 75771	—
Reactant	4-Amino-1-Boc-piperidine	HCID 1268291	—
Reactant	4-(3,3-Dimethyl-butoxy)-1H-indole-2-carboxylic acid {1-[2-(4-hydroxy-piperidin-1-yl)-ethyl]-piperidin-4-yl}-amide dihydrochloride	HCID 66841315	—
Solvent	Dichloromethane	HCID 6344	—
Product	4-[(4-Cyclobutylmethoxy-1H-indole-2-carbonyl)-amino]-piperidine-1-carboxylic acid tert-butyl ester	HCID 66841396	—

Reaction Steps

To a solution of 4-cyclobutylmethoxy-1H-indole-2-carboxylic acid (82) from example 34 (2.2 g, 8.97 mmol) in 20 ml of DCM is added 4-amino-piperidine-1-carboxylic acid tert-butyl ester (1.98 g, 9.87 mmol), HOBT (1.37 g, 8.97 mmol), triethylamine (2.5 ml, 17.94 mmol) and EDC (1.72 g, 8.97 mmol). The mixture is stirred at room temperature over night. It is then washed with 2N—NaOH and brine, dried over anhydrous sodium sulphate and evaporated to give a yellow powder. The crude material is purified by chromatography on silicagel using hexane and EtOAc (from 0% to 20%).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07858781B2
Source dataset	uspto-grants-2010_12
ORD ID	ord-b8ed1866ee674b33985ecb3e7f8d3358
Source note	uspto-grants-2010_12