Chloroacetyl chloride → (2R,5R)-4-{2-[6-(1,1-Difluoro-butyl)-3,3-dimethyl-2,3-dihydro-pyrrolo[3,2-b]pyridin-1-yl]-2-oxo-ethyl}-5-hydroxymethyl-2-methyl-piperazine-1-carboxylic acid tert-butyl ester

Participants

Role	Name	HCID	Charge
Reactant	Chloroacetyl chloride	HCID 6577	—
Reactant	Diisopropylethylamine	HCID 81531	—
Reactant	6-(1,1-difluoro-butyl)-3,3-dimethyl-2,3-dihydro-1H-pyrrolo[3,2-b]pyridine	HCID 70980509	—
Reactant	(2R,5R)-tert-Butyl 5-(hydroxymethyl)-2-methylpiperazine-1-carboxylate	HCID 71003242	—
Product	(2R,5R)-4-{2-[6-(1,1-Difluoro-butyl)-3,3-dimethyl-2,3-dihydro-pyrrolo[3,2-b]pyridin-1-yl]-2-oxo-ethyl}-5-hydroxymethyl-2-methyl-piperazine-1-carboxylic acid tert-butyl ester	HCID 70980732	60%

Reaction Steps

Following methods similar to those described in Preparation 203 or General Procedure 5, starting from (2R,5R)-5-hydroxymethyl-2-methyl-piperazine-1-carboxylic acid tert-butyl ester (0.69 g, 3.0 mmol), 6-(1,1-difluoro-butyl)-3,3-dimethyl-2,3-dihydro-1H-pyrrolo[3,2-b]pyridine, chloroacetyl chloride (185 μL, 2.3 mmol) and DIPEA (1.42 mL, 8.4 mmol), gave the title compound (0.61 g, 60%). MS: [M+H]+=511.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09018214B2
Source dataset	uspto-grants-2015_04
ORD ID	ord-0b3d79ba6c564607829aaa9e02c0a9e8
Source note	uspto-grants-2015_04