Cyclohexene oxide → trans-2-[(6-Bromopyridin-3-yl)oxy]cyclohexanol

HRID 2360313Notes

Reaction equation

HRID 2360313 reaction equation
Br[C:2]1[CH:14]=[CH:13][C:5]([O:6][C@@H]2CCC[C@H]2O)=[CH:4][C:3]=1F.[Br:16][C:17]1[N:22]=[CH:21][C:20]([OH:23])=[CH:19][CH:18]=1.C12OC1CCCC2>>[Br:16][C:17]1[N:22]=[CH:21][C:20]([O:23][C@@H:4]2[CH2:3][CH2:2][CH2:14][CH2:13][C@H:5]2[OH:6])=[CH:19][CH:18]=1

Participants

4

Reactant 3

HCID 9246Cyclohexene oxideHCID 27628652-Bromo-5-hydroxypyridineHCID 67192636trans-2-(4-Bromo-3-fluorophenoxy)cyclopentanol

Product 1

HCID 86653040trans-2-[(6-Bromopyridin-3-yl)oxy]cyclohexanol

Procedure

The title compound of Step 1 was prepared according to the general procedure for the synthesis of trans-2-(4-bromo-3-fluorophenoxy)cyclopentanol in Preparation 3, except that 6-bromopyridin-3-ol was used instead of 4-bromo-3-fluorophenol, and 7-oxabicyclo[4.1.0]heptane in place of 6-oxabicyclo[3.1.0]hexane. The crude product (preparation run in four batches) was recrystallized from heptane to provide trans-2-[(6-bromopyridin-3-yl)oxy]cyclohexanol as an off-white solid. Yield: 11.09 g, 40.75 mmol, 46%. 1H NMR (500 MHz, CDCl3) δ 1.27-1.46 (m, 4H), 1.76-1.80 (m, 2H), 2.09-2.13 (m, 2H), 2.41 (d, J=2.6 Hz, 1H), 3.74 (m, 1H), 4.00 (m, 1H), 7.17 (dd, J=8.7, 3.1 Hz, 1H), 7.37 (d, J=8.5 Hz, 1H), 8.10 (d, J=3.0 Hz, 1H).

Workup

  1. customThe title compound of Step 1 was prepared
  2. customThe crude product (preparation run in four batches) was recrystallized from heptane

Sources & evidence

ORD record
ord-a21909f0052a4f25890634ae92c31279
Source dataset
uspto-grants-2014_04
Patent number
US08686043B2

Reaction notes

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