5-phenyl-3-(1-tosyl-2-(S)-pyrrolidinylmethoxy)pyridine → 5-phenyl-3-(2-(S)-pyrrolidinylmethoxy)pyridine

HRID 1780325Notes

Reaction equation

[C:1]1([C:7]2[CH:8]=[C:9]([O:13][CH2:14][C@@H:15]3[CH2:19][CH2:18][CH2:17][N:16]3S(C3C=CC(C)=CC=3)(=O)=O)[CH:10]=[N:11][CH:12]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1>Br.CC(O)=O>[C:1]1([C:7]2[CH:8]=[C:9]([O:13][CH2:14][C@@H:15]3[CH2:19][CH2:18][CH2:17][NH:16]3)[CH:10]=[N:11][CH:12]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

Conditions

Temperature: 40 °C

Procedure

The 5-phenyl-3-(1-tosyl-2-(S)-pyrrolidinylmethoxy)pyridine from the previous step was dissolved in HBr/HOAc, and the reaction was stirred at room temperature for 16 hours and at 40° C. for 4 hours. The volatiles were removed under vacuum, and the residue was chromatographed on a silica gel column, eluting with chloroform/methanol 10/1.5 to afford the title compound (57 mg). MS (DCI/NH3) m/z 255 (M+H)+. 1H NMR (CDCl3, 300 MHz) δ: 1.54-2.12 (m, 5H), 2.95-3.13 (m, 2H), 3.54-3.66 (m, 1H), 3.94-4.08 (m, 2H), 7.36-7.52 (m, 4H), 7.54-7.62 (m, 2H), 8.29 (d, J=3, 1H), 8.46 (d, J=2, 1H).

Workup

customThe volatiles were removed under vacuum
customthe residue was chromatographed on a silica gel column
washeluting with chloroform/methanol 10/1.5

Sources & evidence

ORD record: ord-32da3808e69b4550b8feabbd93266820
Source dataset: uspto-grants-1997_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05629325

Reaction notes

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