(+-)-3-Quinuclidinol → HCID 11301388, compound

HRID 1294651Notes

Reaction equation

[OH:1][CH:2]1[CH:7]2[CH2:8][CH2:9][N:4]([CH2:5][CH2:6]2)[CH2:3]1.[CH:10]1[C:15]([OH:16])=[CH:14][CH:13]=[C:12]([O:17][C:18]2[CH:23]=[CH:22][C:21](O)=[CH:20][CH:19]=2)[CH:11]=1>>[N:4]12[CH2:9][CH2:8][CH:7]([CH2:6][CH2:5]1)[CH:2]([O:1][C:21]1[CH:22]=[CH:23][C:18]([O:17][C:12]3[CH:13]=[CH:14][C:15]([OH:16])=[CH:10][CH:11]=3)=[CH:19][CH:20]=1)[CH2:3]2

Participants

Reactant 2

HCID 15381(+-)-3-Quinuclidinol

HCID 160694,4'-Dihydroxydiphenyl ether

Product 1

HCID 11301388HCID 11301388, compound

Procedure

3-Hydroxy quinuclidine (Aldrich, 254 mg, 2 mmol) was treated with 4,4′-dihydroxydiphenyl ether (TCl, 202 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. 0.2) as oil (210 mg, yield, 68%). 1H NMR (MeOH-d4, 300 MHz) δ 1.40–1.55 (m, 1H), 1.60–1.87 (m, 2H), 1.98–2.15 (m, 1H), 2.20–2.25 (m, 1H), 2.75–2.98 (m, 5H), 3.20–3.30 (m, 1H), 4.45(m, 1H), 6.62–6.96 (m, 8(DCl/NH3) m/z 312 (M+H)+.

Workup

customThe title compound was purified by chromatography (SiO2, CH2Cl2:MeOH:NH3 H2O, 90:10:1, Rf. 0.2) as oil (210 mg, yield, 68%)

Sources & evidence

ORD record: ord-ddbfeac13797448692ce6a0983cb94c0
Source dataset: uspto-grants-2007_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07241773B2

Reaction notes

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