2,6-Bis(bromomethyl)pyridine → (S)-2-Bromomethyl-6-(tetrahydrofuran-3-yloxymethyl)pyridine

HRID 2096658Notes

Reaction equation

HRID 2096658 reaction equation
Br[CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([CH2:9][Br:10])[N:4]=1.[O:11]1[CH2:15][CH2:14][C@H:13]([OH:16])[CH2:12]1>>[Br:10][CH2:9][C:5]1[CH:6]=[CH:7][CH:8]=[C:3]([CH2:2][O:16][C@H:13]2[CH2:14][CH2:15][O:11][CH2:12]2)[N:4]=1

Participants

3

Reactant 2

HCID 6036102,6-Bis(bromomethyl)pyridineHCID 2733227(S)-(+)-3-Hydroxytetrahydrofuran

Product 1

HCID 66718357(S)-2-Bromomethyl-6-(tetrahydrofuran-3-yloxymethyl)pyridineYield 24%

Procedure

Prepared from 2,6-bis(bromomethyl)pyridine and (S)-tetrahydrofuran-3-ol by the alkylation method described for the final step of Example 32 to give the title compound (24%); NMR δH (400 MHz, CDCl3) 7.70 (1H, t, J 7.5 Hz), 7.39 (1H, d, J 7.5 Hz), 7.34 (1H, d, J 7.5 Hz), 4.67-4.59 (2H, m), 4.52 (2H, s), 4.31-4.26 (1H, m) 3.98-3.81 (4H, m), 2.11-1.99 (2H, m); (M+H)+ 272, 274.

Sources & evidence

ORD record
ord-9077d0971097421f9341652d36f0ed47
Source dataset
uspto-grants-2013_05
Patent number
US08450328B2

Reaction notes

Loading…