Diisopropylethylamine → ((S)-1-{1-[2-(3-Methyl-[1,2,4]-oxadiazol-5-yl)-phenyl]-methanoyl}-piperidin-2-ylmethyl)-carbamic acid tert butyl ester

Participants

Role	Name	HCID	Charge
Reactant	Diisopropylethylamine	HCID 81531	—
Reactant	tert-butyl N-{[(2S)-piperidin-2-yl]methyl}carbamate	HCID 1501973	—
Reactant	Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)	HCID 9886157	—
Reactant	2-(3-Methyl-1,2,4-oxadiazol-5-yl)benzoic acid	HCID 23146305	—
Solvent	Dimethylformamide	HCID 6228	—
Product	((S)-1-{1-[2-(3-Methyl-[1,2,4]-oxadiazol-5-yl)-phenyl]-methanoyl}-piperidin-2-ylmethyl)-carbamic acid tert butyl ester	HCID 86593675	—

Reaction Conditions

Temperature	90 °C

Reaction Steps

A mixture of (S)-1-piperidin-2-ylmethyl-carbamic acid tert butyl ester (2.0 g) and 2-(3-methyl-[1,2,4]oxadiazol-5-yl)-benzoic acid (1.9) in dimethylformamide (10 ml containing diisopropylethylamine (2.4 ml) was treated with [O-(7-azabenzotriazol-1-yl)-1,1,3,3-tetramethyluronium hexafluorophosphate] (3.55 g) and stirred at 90° C. for 16 hours. Solvent was removed at reduced pressure and the residue column chromatographed (silica gel, diethyl ether eluant) to give the title compound (3.4 g).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07741329B2
Source dataset	uspto-grants-2010_06
ORD ID	ord-92e42c39a1fb42739a6c7b48039086c7
Source note	uspto-grants-2010_06