Methanol → 4-{4-[(3R)-1-azabicyclo[2.2.2]oct-3-yloxy]phenoxy}phenol Fumarate

HRID 1294654Notes

Reaction equation

HRID 1294654 reaction equation
[N:1]12[CH2:8][CH2:7][CH:4]([CH2:5][CH2:6]1)[C@@H:3]([O:9][C:10]1[CH:23]=[CH:22][C:13]([O:14][C:15]3[CH:20]=[CH:19][C:18]([OH:21])=[CH:17][CH:16]=3)=[CH:12][CH:11]=1)[CH2:2]2.CO.[C:26]([OH:33])(=[O:32])/[CH:27]=[CH:28]/[C:29]([OH:31])=[O:30]>C(OCC)(=O)C>[C:26]([OH:33])(=[O:32])/[CH:27]=[CH:28]/[C:29]([OH:31])=[O:30].[N:1]12[CH2:8][CH2:7][CH:4]([CH2:5][CH2:6]1)[C@@H:3]([O:9][C:10]1[CH:11]=[CH:12][C:13]([O:14][C:15]3[CH:20]=[CH:19][C:18]([OH:21])=[CH:17][CH:16]=3)=[CH:22][CH:23]=1)[CH2:2]2

Participants

5

Reactant 3

HCID 887MethanolHCID 444972Fumaric AcidHCID 117713334-{4-[(3R)-1-azabicyclo[2.2.2]oct-3-yloxy]phenoxy}phenol

Product 1

HCID 695194544-{4-[(3R)-1-azabicyclo[2.2.2]oct-3-yloxy]phenoxy}phenol FumarateYield 62%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

The product of Example 9A (48 mg, 0.15 mmol) in ethyl acetate:MeOH (3 mL, 10:1) was treated with fumaric acid (Aldrich, 17.4 mg, 0.15 mmol) at room temperature and stirred overnight to provide the title compound as a solid (34 mg, yield, 62%). 1H NMR (MeOH-d4, 300 MHz) δ 1.73–2.19 (m, 3H), 2.21–2.40 (m, 1H), 2.41–2.56 (m, 1H), 3.03–3.27 (m, 5H), 3.59–3.73 (m, 1H), 4.67 (m, 1H), 6.67 (s, 1H), 6.67–6.98 (m, 8H) ppm. MS (DCl/NH3) m/z 312 (M+H)+. Anal. Calculated for C19H21NO3.0.5C4H4O4. 0.35H2O C, 67.13; H, 6.36; N, 3.73. Found: C, 67.04; H, 6.46; N, 3.75.

Sources & evidence

ORD record
ord-1f25094a83684f5790f3ec26ed7a15d6
Source dataset
uspto-grants-2007_07
Patent number
US07241773B2

Reaction notes

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