Reaction equation
[OH:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([CH2:12][N:13]1[CH2:16][CH:15]([C:17]([O:19][CH3:20])=[O:18])[CH2:14]1)[CH:6]=[CH:5]2.[F:21][C:22]([F:31])([F:30])[CH:23]1[CH2:28][CH2:27][CH:26](O)[CH2:25][CH2:24]1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C>C1(C)C=CC=CC=1>[F:21][C:22]([F:31])([F:30])[CH:23]1[CH2:28][CH2:27][CH:26]([O:1][C:2]2[CH:3]=[C:4]3[C:9](=[CH:10][CH:11]=2)[CH:8]=[C:7]([CH2:12][N:13]2[CH2:16][CH:15]([C:17]([O:19][CH3:20])=[O:18])[CH2:14]2)[CH:6]=[CH:5]3)[CH2:25][CH2:24]1Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
To a vial was added methyl 1-((6-hydroxynaphthalen-2-yl)methyl)azetidine-3-carboxylate (271 mg, 1.0 mmol), 4-(trifluoromethyl)cyclohexanol (252 mg, 1.5 mmol, 1.5 equiv), PPh3 (524 mg, 2.0 mmol, 2.0 equiv) and toluene (0.8 mL) under N2 atmosphere. While stirring, DIAD (404 mg, 2.0 mmol, 2.0 equiv) was added to the reaction mixture quickly at r.t and stirred for 10 min. The reaction mixture was then purified by silica gel chromatography (PE:EA=5:1) to give the title compound (114 mg, 28%) as a slight yellow oil. ESI-MS (M+1)+: 408.2. 1H NMR (400 MHz, CD3OD) δ: 7.76 (d, 1H), 7.70 (d, 1H), 7.66 (s, 1H), 7.36 (dd, 1H), 7.24 (d, 1H), 7.17 (dd, 1H), 4.86-4.76 (m, 1H), 3.74 (s, 2H), 3.70 (s, 3H), 3.56-3.51 (m, 2H), 3.32-3.34 (m, 3H), 2.33-2.22 (m, 1H), 2.20 (d, 2H), 1.82-1.67 (m, 6H).
Workup
- stirringstirred for 10 min
- customThe reaction mixture was then purified by silica gel chromatography (PE:EA=5:1)
Sources & evidence
- ORD record
- ord-613c29a0d763459eab99e5ffa3d40465
- Source dataset
- uspto-grants-2015_11
- Patent number
- US09186367B2
Linked notes
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