(+-)-3-Quinuclidinol → HCID 69434105, compound

HRID 969978Notes

Reaction equation

HRID 969978 reaction equation
[OH:1][CH: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]([C:17]2[CH:22]=[CH:21][C:20](O)=[CH:19][CH:18]=2)=[CH:13][CH:12]=1>>[I:10][C:11]1[CH:12]=[CH:13][C:14]([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:15][CH:16]=1

Participants

3

Reactant 2

HCID 15381(+-)-3-QuinuclidinolHCID 20640304-Hydroxy-4'-iodobiphenyl

Product 1

HCID 69434105HCID 69434105, compound

Procedure

3-Hydroxy quinuclidine (Aldrich, 508 mg, 4 mmol) was coupled with 4′-iodo-1,1′-biphenyl-4-ol (Avacado, 592 mg, 2 mmol) according to the procedure of Example 5A. The title product was purified by chromatography (SiO2, CH2Cl2:MeOH:NH3.H2O, 90:10:1, Rf. 0.30) as solid (480 mg, yield, 59%). 1H NMR (MeOH-d4, 300 MHz) δ 1.43-1.57 (m, 1H), 1.62-1.88 (m, 2H), 1.97-2.12 (m, 1H), 2.14-2.21 (m, 1H), 2.72-3.00 (m, 5H), 3.31-3.43 (m, 1H), 4.51-4.60 (m, 1H), 6.98 (d, J=8.8 Hz, 2H), 7.35 (d, J=8.5 Hz, 2H), 7.53 (d, J=8.8 Hz, 2H), 7.74 (d, J=8.5 Hz, 2H) ppm. MS (DCl/NH3) m/z 406 (M+H)+.

Workup

  1. customThe title product was purified by chromatography (SiO2, CH2Cl2:MeOH:NH3.H2O, 90:10:1, Rf. 0.30) as solid (480 mg, yield, 59%)

Sources & evidence

ORD record
ord-da8bc08989fe427f864a96245e0c6dd9
Source dataset
uspto-grants-2007_12
Patent number
US07309699B2

Reaction notes

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