(R)-(+)-3-Aminoquinuclidine Dihydrochloride → HCID 69794740, compound

HRID 2181669Notes

Reaction equation

HRID 2181669 reaction equation
[CH2:1]([O:3][CH:4]([O:17][CH2:18][CH3:19])[C:5]1[O:6][C:7]2[CH:13]=[C:12]([C:14]([OH:16])=O)[CH:11]=[CH:10][C:8]=2[CH:9]=1)[CH3:2].[ClH:20].Cl.[NH2:22][C@@H:23]1[CH:28]2[CH2:29][CH2:30][N:25]([CH2:26][CH2:27]2)[CH2:24]1>>[ClH:20].[N:25]12[CH2:30][CH2:29][CH:28]([CH2:27][CH2:26]1)[C@@H:23]([NH:22][C:14]([C:12]1[CH:11]=[CH:10][C:8]3[CH:9]=[C:5]([CH:4]([O:3][CH2:1][CH3:2])[O:17][CH2:18][CH3:19])[O:6][C:7]=3[CH:13]=1)=[O:16])[CH2:24]2

Participants

3

Reactant 2

HCID 12494972(R)-(+)-3-Aminoquinuclidine DihydrochlorideHCID 69795068HCID 69795068, compound

Product 1

HCID 69794740HCID 69794740, compoundYield 70%

Procedure

2-(Diethoxymethyl)-1-benzofuran-6-carboxylic acid (264 mg, 1.0 mmol) is coupled with (R)-3-aminoquinuclidine dihydrochloride (219 mg, 1.1 mmol) and salt made according to Method A with non-critical changes to afford 286 mg (70%) of N-[(3R)-1-azabicyclo[2.2.2]oct-3-yl]-2-(diethoxymethyl)-1-benzofuran-6-carboxamide hydrochloride as a white solid. HRMS (FAB) calcd for C21H28N2O4+H: 373.2127, found 373.2121 (M+H)+.

Sources & evidence

ORD record
ord-0bdd38a94c584b6da33e82cc8d463465
Source dataset
uspto-grants-2005_05
Patent number
US06894042B2

Reaction notes

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