Hydrochloric Acid → 2-(R)-(3-(S)-((4-(3-Phenylpropyl)piperidin-1-yl)methyl)-4 (S)-(3-fluorophenyl)pyrrolidin-1-yl)-3-(cyclobutyl)propanoic acid, benzyl ester

Participants

Role	Name	HCID	Charge
Reactant	Hydrochloric Acid	HCID 313	—
Reactant	4-(3-Phenylpropyl)piperidine	HCID 87678	—
Reactant	(R)-3-Cyclobutyl-2-{(S)-3-(3-fluoro-phenyl)-4-[4-(3-phenyl-propyl)-piperidin-1-ylmethyl]-pyrrolidin-1-yl}-propionic acid	HCID 20672386	—
Product	2-(R)-(3-(S)-((4-(3-Phenylpropyl)piperidin-1-yl)methyl)-4 (S)-(3-fluorophenyl)pyrrolidin-1-yl)-3-(cyclobutyl)propanoic acid, benzyl ester	HCID 131722805	102.1%

Reaction Steps

The title compound was prepared from 23.2 mg (0.052 mmol) of 2-(R)-(3-(R)-formyl-4-(S)-(3-fluorophenyl)pyrrolidin-1-yl)-3-(cyclobutyl)propanoic acid, benzyl ester (from EXAMPLE 26, Step A) and 12.8 mg (0.052 mmol) of 4-(3-phenylpropyl)piperidine.HCl using a procedure analogous to that described in EXAMPLE 1, Step J to provide 31.7 mg (96%) of the title compound: RF: 0.57 (1:1 v/v hexanes/EtOAc); 1H NMR (300 MHz) δ 1.13-3.27 (m, 33H), 5.14 (s, 2H), 6.86-6.99 (m, 3H), 7.14-7.38 (m, 11H).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US06265434B1
Source dataset	uspto-grants-2001_07
ORD ID	ord-6bb0f63b66344746b5f41e691ee740ef
Source note	uspto-grants-2001_07