(+-)-3-Quinuclidinol → HCID 11347518, compound

HRID 1294649Notes

Reaction equation

[OH:1][CH:2]1[CH:7]2[CH2:8][CH2:9][N:4]([CH2:5][CH2:6]2)[CH2:3]1.[F:10][C:11]1[CH:24]=[CH:23][C:14]([O:15][C:16]2[CH:21]=[CH:20][C:19](O)=[CH:18][CH:17]=2)=[CH:13][CH:12]=1>>[F:10][C:11]1[CH:24]=[CH:23][C:14]([O:15][C:16]2[CH:21]=[CH:20][C:19]([O:1][CH:2]3[CH:7]4[CH2:8][CH2:9][N:4]([CH2:5][CH2:6]4)[CH2:3]3)=[CH:18][CH:17]=2)=[CH:13][CH:12]=1

Participants

Reactant 2

HCID 15381(+-)-3-Quinuclidinol

HCID 129406244-(4-Fluorophenoxy)phenol

Product 1

HCID 11347518HCID 11347518, compound

Procedure

3-Hydroxy quinuclidine (Aldrich, 254 mg, 2 mmol) was treated with 4-(4-fluoro-phenoxy)-phenol (Aldrich, 205 mg, 1 mmol) according to the procedure of Example 1A. The title compound was purified by chromatography (SiO2, CH2Cl2:MeOH:NH3.H2O, 90:10:1, Rf. 0.45) as oil (230 mg, yield, 73%). 1H NMR (MeOH-d4, 300 MHz) δ 1.40–1.52 (m, 1H), 1.64–1.87 (m, 2H), 1.98–2.15 (m, 1H), 2.20–2.25 (m, 1H), 2.66–3.00 (m, 5H), 3.30–3.40 (m, 1H), 4.48(m, 1H), 6.61 (dt, J=10.5, 2.4 Hz, 1H), 6.71(dd, J=8.1, 2.3 Hz, 1H), 6.76 (tdd, J=8.4, 2.3, 1.0 Hz, 1H), 6.87–7.00 (m, 3H), 7.22–7.32 (m, 2H) ppm. MS (DCl/NH3) m/z 314 (M+H)+.

Workup

customThe title compound was purified by chromatography (SiO2, CH2Cl2:MeOH:NH3.H2O, 90:10:1, Rf. 0.45) as oil (230 mg, yield, 73%)

Sources & evidence

ORD record: ord-1b0527b62bfc4280bcdab50bc9d68112
Source dataset: uspto-grants-2007_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07241773B2

Reaction notes

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