trans-4-[(6-Bromopyridin-3-yl)oxy]tetrahydrofuran-3-ol → trans-4-[(6-Bromopyridin-3-yl)oxy]tetrahydrofuran-3-yl methanesulfonate
Reaction equation
[CH3:1][S:2](O[C@@H]1CCC[C@H]1OC1C=CC(Br)=CC=1)(=[O:4])=[O:3].[Br:19][C:20]1[N:25]=[CH:24][C:23]([O:26][C@@H:27]2[CH2:31][O:30][CH2:29][C@H:28]2[OH:32])=[CH:22][CH:21]=1>>[CH3:1][S:2]([O:32][C@H:28]1[C@H:27]([O:26][C:23]2[CH:24]=[N:25][C:20]([Br:19])=[CH:21][CH:22]=2)[CH2:31][O:30][CH2:29]1)(=[O:4])=[O:3]Participants
3
Procedure
The title compound of Step 2 was prepared according to the general procedure for the synthesis of trans-2-(4-bromophenoxy)cyclopentyl methanesulfonate in Example 5, except that trans-4-[(6-bromopyridin-3-yl)oxy]tetrahydrofuran-3-ol was used instead of trans-2-(4-bromophenoxy)cyclopentanol. The product was obtained as a solid. Yield: 5.95 g, 17.6 mmol, 87%. 1H NMR (400 MHz, CDCl3) δ 3.07 (s, 3H), 3.94 (br dd, J=10.5, 1.8 Hz, 1H), 4.00 (m, 1H), 4.11 (dd, J=11.1, 4.1 Hz, 1H), 4.18 (dd, J=10.6, 4.5 Hz, 1H), 4.97 (br d, J=4.4 Hz, 1H), 5.13 (br d, J=3.8 Hz, 1H), 7.19 (dd, J=8.7, 3.2 Hz, 1H), 7.35 (dd, J=8.7, 0.5 Hz, 1H), 8.04 (dd, J=3.2, 0.5 Hz, 1H).
Workup
- customThe product was obtained as a solid
Sources & evidence
- ORD record
- ord-f8dc92e793a5466d94b7685a95969e32
- Source dataset
- uspto-grants-2014_04
- Patent number
- US08686043B2
Reaction notes
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