p-Diiodobenzene → HCID 69434720, compound

HRID 1294666Notes

Reaction equation

[OH:1][C@@H:2]1[CH:7]2[CH2:8][CH2:9][N:4]([CH2:5][CH2:6]2)[CH2:3]1.[I:10][C:11]1[CH:16]=[CH:15][C:14](I)=[CH:13][CH:12]=1>>[I:10][C:11]1[CH:16]=[CH:15][C:14]([O:1][C@@H:2]2[CH:7]3[CH2:8][CH2:9][N:4]([CH2:5][CH2:6]3)[CH2:3]2)=[CH:13][CH:12]=1

Participants

Reactant 2

HCID 12208p-Diiodobenzene

HCID 914043-Quinuclidinol, (-)-

Product 1

HCID 69434720HCID 69434720, compound

Procedure

3-(R)-Hydroxyquinuclidine (the product of Reference Example 1, 0.64 g, 5.0 mmol) was treated with 1,4-diiodobenzene (1.98 g, 6.0 mmol) according to the procedure of Example 14A. The title compound was purified by flash chromatography (SiO2, CH2Cl2:MeOH:NH3.H2O, 90:10:1, Rf. 0.30) as a solid (0.50 g, yield, 15%). 1H NMR (MeOH-d4, 300 MHz) δ 1.41–1.54 (m, 1H), 1.59–1.73 (m, 1H), 1.73–1.86 (m, 1H), 1.92–2.05 (m, 1H), 2.09–2.17 (m, 1H), 2.71–2.97 (m, 5H), 3.24–3.34 (m, 1H), 4.44–4.52 (m, 1H), 6.72 (d, J=8.8 Hz, 2H), 7.55 (d, J=9.2 Hz, 2H) ppm. MS (DCl/NH3): m/z 330 (M+H)+.

Workup

customThe title compound was purified by flash chromatography (SiO2, CH2Cl2:MeOH:NH3.H2O, 90:10:1, Rf. 0.30) as a solid (0.50 g, yield, 15%)

Sources & evidence

ORD record: ord-98cf5324e5e640dc88d9ed3c497cc78d
Source dataset: uspto-grants-2007_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07241773B2

Reaction notes

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