Triethylamine → 2-(3,5-Bis-trifluoromethyl-phenyl)-n-[(3s,4r)-1-(4-ethynyl-cyclohexanecarbonyl)-4-phenyl-pyrrolidin-3-yl]-n-methyl-isobutyramide

Participants

Role	Name	HCID	Charge
Reactant	Triethylamine	HCID 8471	—
Reactant	Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphate	HCID 151348	—
Reactant	trans-4-Ethynylcyclohexanecarboxylic acid	HCID 19373388	—
Reactant	Rac-2-(3,5-bis-trifluoromethyl-phenyl)-n-methyl-n-((3s,4r)-4-phenyl-pyrrolidin-3-yl)-isobutyramide	HCID 59840126	—
Solvent	Tetrahydrofuran	HCID 8028	—
Product	2-(3,5-Bis-trifluoromethyl-phenyl)-n-[(3s,4r)-1-(4-ethynyl-cyclohexanecarbonyl)-4-phenyl-pyrrolidin-3-yl]-n-methyl-isobutyramide	HCID 59840125	54%

Reaction Steps

To a stirred solution of 4-ethynyl-cyclohexanecarboxylic acid (commercially available) (6.5 mg, 0.043 mmol) in THF (2 ml) at RT were added Et3N (12 μl, 0.086 mmol), BOP (25 mg, 0.057 mmol) and rac-2-(3,5-bis-trifluoromethyl-phenyl)-N-methyl-N-((3S,4R)-4-phenyl-pyrrolidin-3-yl)-isobutyramide (Intermediate VII-1) (20 mg, 0.043 mmol). Stirring was continued at 40° C. for 48 hours. Concentration and purification by preparative HPLC afforded 13.7 mg (54%) of the title compound.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07893062B2
Source dataset	uspto-grants-2011_02
ORD ID	ord-7b92719049ae4935a58066e6e89a2453
Source note	uspto-grants-2011_02