Hydrochloric Acid → tert-butyl (1S,2S,4S)-4-amino-1-benzyl-2-hydroxy-5-[4-(2-pyridinyl)phenyl]pentylcarbamate

Participants

Role	Name	HCID	Charge
Reactant	Hydrochloric Acid	HCID 313	—
Reactant	Benzyl (1S,3S,4S)-4-[(tert-butoxycarbonyl)amino]-3-hydroxy-5-phenyl-1-[4-(2-pyridinyl)benzyl]pentylcarbamate	HCID 11548871	—
Catalyst	Palladium hydroxide	HCID 9942167	—
Solvent	Methanol	HCID 887	—
Solvent	Ethyl Acetate	HCID 8857	—
Product	tert-butyl (1S,2S,4S)-4-amino-1-benzyl-2-hydroxy-5-[4-(2-pyridinyl)phenyl]pentylcarbamate	HCID 11605032	—

Reaction Conditions

Temperature	25 °C

Reaction Steps

A solution of the product of Example 1C (4.2 g, 7.0 mmol) in a mixture of methanol (35 mL) and ethyl acetate (35 mL) was treated with Pd(OH)2 on carbon (1.4 g, 20% Pd by wt.) and HCl solution (1.8 mL, 4N in dioxane), and the reaction was stirred under a hydrogen atmosphere (balloon pressure) for 16 hours at 25° C. The reaction mixture was filtered through a bed of celite®, rinsed with methanol and concentrated to give the title compound as the hydrochloride salt (3.7 g).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07834043B2
Source dataset	uspto-grants-2010_11
ORD ID	ord-1fce14efd3c740aa8ca9407d8fd9df06
Source note	uspto-grants-2010_11