Triphenylphosphine → 3-[(4'-Nitro-1,1'-biphenyl-4-yl)oxy]quinuclidine
Reaction equation
[N:1]12[CH2:8][CH2:7][CH:4]([CH2:5][CH2:6]1)[CH:3]([OH:9])[CH2:2]2.[N+:10]([C:13]1[CH:18]=[CH:17][C:16]([C:19]2[CH:24]=[CH:23][C:22](O)=[CH:21][CH:20]=2)=[CH:15][CH:14]=1)([O-:12])=[O:11].CC(OC(/N=N/C(OC(C)C)=O)=O)C.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>O1CCCC1>[N+:10]([C:13]1[CH:14]=[CH:15][C:16]([C:19]2[CH:24]=[CH:23][C:22]([O:9][CH:3]3[CH:4]4[CH2:7][CH2:8][N:1]([CH2:6][CH2:5]4)[CH2:2]3)=[CH:21][CH:20]=2)=[CH:17][CH:18]=1)([O-:12])=[O:11]Participants
Procedure
3-Quinuclidinol (Aldrich, 254 mg, 2 mmol) in tetrahydrofuran (anhydrous, Aldrich, 10 mL) was treated with 4′-nitro-1,1′-biphenyl-4-ol (TCl, 215 mg, 1 mmol) with DIAD (di-isopropyl azadicarboxylate, Aldrich, 404 mg, 2 mmol) and triphenylphosphine (Aldrich, 522 mg, 2 mmol) at ambient temperature for two days. The reaction mixture was concentrated. The title product was purified by chromatography (SiO2, CH2Cl2:MeOH:NH3.H2O, 90:10:1, Rf. 0.20) as a solid (200 mg, yield, 62%). 1H NMR (MeOH-d4, 300 MHz) δ 1.45-1.57 (m, 1H), 1.63-1.91 (m, 2H), 1.97-2.12 (m, 1H), 2.17-2.24 (m, 1H), 2.66-3.00 (m, 5H), 3.30-3.41 (m, 1H), 4.56-4.64 (m, 1H), 7.05 (dt, J=8.8, 2.6 Hz, 2H), 7.68 (dt, J=9.2, 2.6 Hz, 2H), 7.82 (dt, J=8.8, 2.7 Hz, 2H), 8.28 (dt, J=8.8, 2.8 Hz, 2H) ppm. MS (DCl/NH3) m/z 325 (M+H)+.
Workup
- concentrationThe reaction mixture was concentrated
- customThe title product was purified by chromatography (SiO2, CH2Cl2:MeOH:NH3.H2O, 90:10:1, Rf. 0.20) as a solid (200 mg, yield, 62%)
Sources & evidence
- ORD record
- ord-f6160c129b124cefbad3432ada76d8b3
- Source dataset
- uspto-grants-2007_12
- Patent number
- US07309699B2
Reaction notes
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