Hydrochloric Acid → 5-[(1R)-2-[2-(aminomethyl)pyrrolidin-1-yl]-1-hydroxyethyl]-4-methyl-2-benzofuran-1(3H)-one hydrochloride

HRID 515113Notes

Reaction equation

HRID 515113 reaction equation
C(OC(=O)[NH:7][CH2:8][CH:9]1[CH2:13][CH2:12][CH2:11][N:10]1[CH2:14][C@H:15]([OH:27])[C:16]1[CH:25]=[CH:24][C:19]2[C:20](=[O:23])[O:21][CH2:22][C:18]=2[C:17]=1[CH3:26])(C)(C)C.[ClH:29]>O1CCOCC1>[ClH:29].[NH2:7][CH2:8][CH:9]1[CH2:13][CH2:12][CH2:11][N:10]1[CH2:14][C@@H:15]([C:16]1[CH:25]=[CH:24][C:19]2[C:20](=[O:23])[O:21][CH2:22][C:18]=2[C:17]=1[CH3:26])[OH:27]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 131733295tert-Butyl ({1-[(2R)-2-hydroxy-2-(4-methyl-1-oxo-1,3-dihydro-2-benzofuran-5-yl)ethyl]pyrrolidin-2-yl}methyl)carbamate

Product 1

HCID 904097625-[(1R)-2-[2-(aminomethyl)pyrrolidin-1-yl]-1-hydroxyethyl]-4-methyl-2-benzofuran-1(3H)-one hydrochloride

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

A suspension of the faster eluting diastereomer of tert-butyl({1-[(2R)-2-hydroxy-2-(4-methyl-1-oxo-1,3-dihydro-2-benzofuran-5-yl)ethyl]pyrrolidin-2-yl}methyl)carbamate (710 mg, 1.82 mmol) in dioxane (2.0 mL) was treated with a solution of hydrochloric acid in dioxane (4.0 M, 2.0 mL). After shaking sixteen hours, the solvents were removed in vacuo to provide 5-[(1R)-2-[2-(aminomethyl)pyrrolidin-1-yl]-1-hydroxyethyl}-4-methyl-2-benzofuran-1(3H)-one hydrochloride which was carried on without purification.

Workup

  1. additionA suspension of the
  2. customthe solvents were removed in vacuo

Sources & evidence

ORD record
ord-553dc0131c9b416da71c1fe93dff5ea7
Source dataset
uspto-grants-2015_08
Patent number
US09108947B2

Reaction notes

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