1,4-Dioxane hydrochloride → (R)-2-Amino-3-(4-fluoro-phenyl)-1-(4-hydroxy-piperidin-1-yl)-propan-1-one hydrochloride

HRID 1872157Notes

Reaction equation

HRID 1872157 reaction equation
C(OC(=O)[NH:7][C@H:8]([CH2:18][C:19]1[CH:24]=[CH:23][C:22]([F:25])=[CH:21][CH:20]=1)[C:9]([N:11]1[CH2:16][CH2:15][CH:14]([OH:17])[CH2:13][CH2:12]1)=[O:10])(C)(C)C.[ClH:27].O1CCOCC1>>[ClH:27].[NH2:7][C@H:8]([CH2:18][C:19]1[CH:20]=[CH:21][C:22]([F:25])=[CH:23][CH:24]=1)[C:9]([N:11]1[CH2:12][CH2:13][CH:14]([OH:17])[CH2:15][CH2:16]1)=[O:10]

Participants

3

Reactant 2

HCID 204431481,4-Dioxane hydrochlorideHCID 21970173[1-(R)-(4-Fluorobenzyl)-2-(4-hydroxypiperidin-1-yl)-2-oxoethyl] carbamic acid tert-butyl ester

Product 1

HCID 67279148(R)-2-Amino-3-(4-fluoro-phenyl)-1-(4-hydroxy-piperidin-1-yl)-propan-1-one hydrochloride

Conditions

Temperature
25 °C

Procedure

(R)-[1-(4-Fluoro-benzyl)-2-(4-hydroxy-piperidin-1-yl)-2-oxo-ethyl]-carbamic acid-tert-butyl ester (2.6 mmol) was dissolved in 4M HCl-dioxane (2 mL) at 0° C. The solution was stirred 2 hours at 25° C., concentrated and the residue triturated with ether. Yield, 920 mg, 124%; HPLC (60/40) 2.23 minutes (98%).

Workup

  1. concentrationconcentrated
  2. customthe residue triturated with ether
  3. customYield

Sources & evidence

ORD record
ord-76ec171bbaf94a03a77f8f651971d846
Source dataset
uspto-grants-2000_08
Patent number
US06107329

Reaction notes

Loading…