Trifluoroacetic acid → (1S,2S)-2-amino-1-((R)-1-benzhydrylpiperidin-2-yl)-3-(3,5-difluorophenyl)propan-1-ol

Participants

Role	Name	HCID	Charge
Reactant	Trifluoroacetic acid	HCID 6422	—
Reactant	(2R,4R)-tert-butyl 2-((1S,2S)-2-(3,5-difluorobenzyl)-3-((S)-4-benzyl-2-oxooxazolidin-3-yl)-1-hydroxy-3-oxopropyl)-4-(allyloxy)pyrrolidine-1-carboxylate	HCID 67316359	—
Reactant	(2S,3S)-2-(3,5-difluorobenzyl)-3-((2R,4R)-4-(allyloxy)-1-(tert-butoxycarbonyl)pyrrolidin-2-yl)-3-hydroxypropanoic acid	HCID 67316915	—
Reactant	(4S,5R)-4-(3,5-difluorobenzyl)-5-((R)-piperidin-2-yl)oxazolidin-2-one	HCID 69195213	—
Solvent	Dichloromethane	HCID 6344	—
Product	(1S,2S)-2-amino-1-((R)-1-benzhydrylpiperidin-2-yl)-3-(3,5-difluorophenyl)propan-1-ol	HCID 58608199	—

Reaction Steps

Step I (6): Preparation of (4S,5R)-4-(3,5-difluorobenzyl)-5-((R)-piperidin-2-yl)oxazolidin-2-one. A solution of (R)-tert-butyl 2-((4S,5S)-4-(3,5-difluorobenzyl)-2-oxooxazolidin-5-yl)piperidine-1-carboxylate (Step I (5), 200 mg) in CH2Cl2 (4 mL) was treated with TFA (2 mL). This reaction mixture was stirred at rt for 1 h. The mixture was then concentrated in vacuo with addition of toluene. 1N HCl solution (50 mL) was added and the mixture was extracted with diethyl ether, neutralized with 50% aqueous NaOH to pH=12. The mixture was extracted with ethyl acetate (50 mL) twice. The combined organic layers were dried (Na2SO4), and concentrated in vacuo to give 132 mg of the title compound:

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07388007B2
Source dataset	uspto-grants-2008_06
ORD ID	ord-9edef0d70569471089261bcc9f512475
Source note	uspto-grants-2008_06