HCID 89634412, compound → HCID 89620108, compound
Reaction equation
[F:1][CH2:2][C@@H:3]1[CH2:7][CH2:6][N:5]([CH2:8][CH2:9][O:10][C:11]2[CH:16]=[CH:15][C:14]([CH:17]3[C:26]([C:27]4[CH:32]=[CH:31][CH:30]=[C:29]([O:33]C5CCCCO5)[CH:28]=4)=[C:25]([CH3:40])[C:24]4[C:19](=[CH:20][CH:21]=[C:22]([O:41]C5CCCCO5)[CH:23]=4)[O:18]3)=[CH:13][CH:12]=2)[CH2:4]1>C(O)(=O)C>[F:1][CH2:2][CH:3]1[CH2:7][CH2:6][N:5]([CH2:8][CH2:9][O:10][C:11]2[CH:16]=[CH:15][C:14]([C@@H:17]3[C:26]([C:27]4[CH:32]=[CH:31][CH:30]=[C:29]([OH:33])[CH:28]=4)=[C:25]([CH3:40])[C:24]4[C:19](=[CH:20][CH:21]=[C:22]([OH:41])[CH:23]=4)[O:18]3)=[CH:13][CH:12]=2)[CH2:4]1Participants
3
Reactant 1
Product 1
Reagents, catalysts & solvents 1
Procedure
A mixture of (3R)-3-(fluoromethyl)-1-(2-(4-(4-methyl-6-((tetrahydro-2H-pyran-2-yl)oxy)-3-(3-((tetrahydro-2H-pyran-2-yl)oxy)phenyl)-2H-chromen-2-yl)phenoxy)ethyl)pyrrolidine (1.87 g, 2.9 mmol) in acetic acid (80% aq., 30 mL) was stirred at room temperature overnight. The acetic acid was removed and the residue was partitioned between ethyl acetate and sat'd aqueous NaHCO3. The organic layer was washed with sat'd aqueous NaHCO3, dried over sodium sulfate, filtered and the solvent removed. The residue was purified by flash chromatography on silica gel (0 to 5% methanol/dichloromethane) to afford 1.1 g of (R)-2-(4-(2-(3-(fluoromethyl)pyrrolidin-1-yl)ethoxy)phenyl)-3-(3-hydroxyphenyl)-4-methyl-2H-chromen-6-ol as a pinkish foam. 1H NMR (DMSO-d6): δ 9.43 (s, 1H), 8.94 (s, 1H), 7.18 (d, 2H), 7.14 (t, 1H), 6.78 (d, 2H), 6.73 (s, 1H), 6.67-6.65 (m, 2H), 6.65 (s, 1H), 6.49-6.45 (m, 2H), 5.83 (s, 1H), 4.35-4.30 (m, 1H), 4.23-4.19 (m, 1H), 3.96 (t, 2H), 2.71 (t, 2H), 2.60 (t, 1H), 2.46-2.40 (m, 3H), 2.36-2.31 (m, 1H), 2.02 (s, 3H), 1.83-1.76 (m, 1H), 1.39-1.30 (m, 1H); LCMS: 476 (M+H)+.