Hydrochloric Acid → (R)-(R)-quinuclidin-3-yl 2-amino-2-phenylacetate bis hydrochloride

HRID 2279936Notes

Reaction equation

HRID 2279936 reaction equation
[N:1]12[CH2:8][CH2:7][CH:4]([CH2:5][CH2:6]1)[C@@H:3]([O:9][C:10](=[O:26])[C@H:11]([NH:18]C(OC(C)(C)C)=O)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[CH2:2]2.[ClH:27].CCOCC>O1CCOCC1>[ClH:27].[ClH:27].[NH2:18][C@H:11]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:10]([O:9][C@@H:3]1[CH:4]2[CH2:5][CH2:6][N:1]([CH2:8][CH2:7]2)[CH2:2]1)=[O:26]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 67607970(R)-((R)-quinuclidin-3-yl) 2-(tert-butoxycarbonylamino)-2-phenylacetate

Product 1

HCID 86720688(R)-(R)-quinuclidin-3-yl 2-amino-2-phenylacetate bis hydrochloride

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A solution of (R)—(R)-quinuclidin-3-yl2-((tert-butoxycarbonyl)amino)-2-phenylacetate I-46 (0.608 g, 1.687 mmol) in anhydrous dioxane (6 mL) was added with 2M HCl in ether (5.2 mL, 10.4 mmol). The reaction mixture was stirred at room temperature for 20 h. The solvent was removed in vacuo to afford the title compound as a white solid (0.564 g, quantitative yield).

Workup

  1. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-e84d8bcb586a481faf81e15354d7d8df
Source dataset
uspto-grants-2015_09
Patent number
US09133185B2

Reaction notes

Loading…