Hydrochloric Acid → 9-[(2R)-2-hydroxy-2-(4-methyl-1-oxo-1,3-dihydro-2-benzofuran-5-yl)ethyl]-9-aza-6-azoniaspiro[4.5]decane chloride

HRID 2281291Notes

Reaction equation

HRID 2281291 reaction equation
[OH:1][C@H:2]([C:21]1[CH:30]=[CH:29][C:24]2[C:25](=[O:28])[O:26][CH2:27][C:23]=2[C:22]=1[CH3:31])[CH2:3][N:4]1[CH2:13][C:8]2([CH2:12][CH2:11][CH2:10][CH2:9]2)[N:7](C(OC(C)(C)C)=O)[CH2:6][CH2:5]1.[ClH:32]>O1CCOCC1>[Cl-:32].[OH:1][C@H:2]([C:21]1[CH:30]=[CH:29][C:24]2[C:25](=[O:28])[O:26][CH2:27][C:23]=2[C:22]=1[CH3:31])[CH2:3][N:4]1[CH2:13][C:8]2([CH2:9][CH2:10][CH2:11][CH2:12]2)[NH2+:7][CH2:6][CH2:5]1

Participants

4

Reactant 2

HCID 313Hydrochloric Acid2×HCID 117642078tert-butyl 9-[(2R)-2-hydroxy-2-(4-methyl-1-oxo-1,3-dihydro-2-benzofuran-5-yl)ethyl]-6,9-diazaspiro[4.5]decane-6-carboxylate

Product 1

HCID 1176420669-[(2R)-2-hydroxy-2-(4-methyl-1-oxo-1,3-dihydro-2-benzofuran-5-yl)ethyl]-9-aza-6-azoniaspiro[4.5]decane chloride

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent3×

Procedure

A suspension of tert-butyl 9-[(2R)-2-hydroxy-2-(4-methyl-1-oxo-1,3-dihydro-2-benzofuran-5-yl)ethyl]-6,9-diazaspiro[4.5]decane-6-carboxylate (80 mg, 0.20 mmol) in dioxane (200 L) was treated with a solution of hydrochloric acid in dioxane (4.0 M, 200 L). After shaking for 3 hours, the solution was treated with additional hydrochloric acid in dioxane (4.0 M, 100 L). After shaking an additional sixteen hours, the solvents were removed in vacuo to provide 9-[(2R)-2-hydroxy-2-(4-methyl-1-oxo-1,3-dihydro-2-benzofuran-5-yl)ethyl]-9-aza-6-azoniaspiro[4.5]decane chloride which was carried on without further purification.

Workup

  1. stirringAfter shaking an additional sixteen hours
  2. customthe solvents were removed in vacuo

Sources & evidence

ORD record
ord-cedb9e72f95f4d738d89e4078461aa31
Source dataset
uspto-grants-2015_09
Patent number
US09139585B2

Reaction notes

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