(+-)-3-Quinuclidinol → HCID 11382911, compound

HRID 1294648Notes

Reaction equation

HRID 1294648 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]([F:27])([F:26])[C:12]1[CH:25]=[CH:24][C:15]([O:16][C:17]2[CH:22]=[CH:21][C:20](O)=[CH:19][CH:18]=2)=[CH:14][CH:13]=1>>[F:10][C:11]([F:26])([F:27])[C:12]1[CH:25]=[CH:24][C:15]([O:16][C:17]2[CH:22]=[CH:21][C:20]([O:1][CH:2]3[CH:7]4[CH2:8][CH2:9][N:4]([CH2:5][CH2:6]4)[CH2:3]3)=[CH:19][CH:18]=2)=[CH:14][CH:13]=1

Participants

3

Reactant 2

HCID 15381(+-)-3-QuinuclidinolHCID 170230p-(4-(Trifluoromethyl)phenoxy)phenol

Product 1

HCID 11382911HCID 11382911, compound

Procedure

3-Hydroxy quinuclidine (Aldrich, 254 mg, 2 mmol) was treated with 4-(4-trifluoromethyl-phenoxy)-phenol (Aldrich, 255 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. 0.50) as oil (180 mg, yield, 49%). H NMR (MeOH-d4, 300 MHz) δ 1.50–1.58 (m, 1H), 1.64–1.85 (m, 2H), 2.00–2.15 (m, 1H), 2.20–2.30 (m, 1H), 2.76–3.10 (m, 5H), 3.38–3.50 (m, 1H), 4.60 (m, 1H), 6.96–7.04 (m, 6H), 7.60 (d, J=8.5 Hz, 2H) ppm. MS (DCl/NH3) m/z 364 (M+H)+.

Workup

  1. customThe title compound was purified by chromatography (SiO2, CH2Cl2:MeOH:NH3.H2O, 90:10:1, Rf. 0.50) as oil (180 mg, yield, 49%)

Sources & evidence

ORD record
ord-5a997f6f92844d01841a8f3c1b72d13f
Source dataset
uspto-grants-2007_07
Patent number
US07241773B2

Reaction notes

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