Reaction equation
[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[O:7][C@H:8]1[CH2:13][CH2:12][C@H:11]([CH2:14][OH:15])[CH2:10][CH2:9]1.[Br:16][C:17]1[CH:22]=[CH:21][C:20](O)=[CH:19][C:18]=1[F:24].BrC1C=CC(OC[C@@H]2CC[C@H](OC3CCCCO3)CC2)=CC=1>>[Br:16][C:17]1[CH:22]=[CH:21][C:20]([O:15][CH2:14][C@H:11]2[CH2:12][CH2:13][C@H:8]([O:7][CH:2]3[CH2:3][CH2:4][CH2:5][CH2:6][O:1]3)[CH2:9][CH2:10]2)=[CH:19][C:18]=1[F:24]Participants
4
Procedure
The title compound (885 mg, 81.6%) was prepared from (+/−)-[trans-4-(tetrahydro-2H-pyran-2-yloxy)cyclohexyl]methanol (600 mg, 2.80 mmol) and 4-bromo-3-fluorophenol (588 mg, 3.08 mmol) by a procedure analogous to that described for (+/−)-2-({cis-4-[(4-bromophenoxy)methyl]cyclohexyl}oxy)tetrahydro-2H-pyran in Example 8, Step C. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 1.03-1.21 (m, 2 H) 1.21-1.36 (m, 1 H) 1.35-1.50 (m, 1 H) 1.49-1.66 (m, 4 H) 1.65-1.99 (m, 5 H) 2.03-2.17 (m, 2 H) 3.44-3.55 (m, 1 H) 3.60 (tt, J=10.98, 4.24 Hz, 1 H) 3.72 (d, J=6.24 Hz, 2 H) 3.86-4.00 (m, 1 H) 4.70-4.80 (m, 1 H) 6.59 (ddd, J=8.88, 2.83, 0.98 Hz, 1 H) 6.68 (dd, J=10.54, 2.73 Hz, 1 H) 7.35-7.44 (m, 1 H)
Sources & evidence
- ORD record
- ord-5655c4a6e9984d76a80b5b98b4b04408
- Source dataset
- uspto-grants-2014_09
- Patent number
- US08846933B2
Linked notes
Loading…