3,5-Dibromopyridine N-oxide → 3-Bromo-5-((S)-1-methyl-pyrrolidin-2-ylmethoxy)-pyridine 1-oxide

Reaction equation

Br[C:2]1[CH:3]=[N+:4]([O-:9])[CH:5]=[C:6]([Br:8])[CH:7]=1.[CH3:10][N:11]1[CH2:15][CH2:14][CH2:13][C@H:12]1[CH2:16][OH:17]>>[CH3:10][N:11]1[CH2:15][CH2:14][CH2:13][C@H:12]1[CH2:16][O:17][C:2]1[CH:3]=[N+:4]([O-:9])[CH:5]=[C:6]([Br:8])[CH:7]=1

Participants

Reactant 2

HCID 6200033,5-Dibromopyridine N-oxide

HCID 643492(2S)-1-Methyl-2-pyrrolidinemethanol

Product 1

HCID 213096723-Bromo-5-((S)-1-methyl-pyrrolidin-2-ylmethoxy)-pyridine 1-oxide

Procedure

A sample of 3,5-dibromopyridine-N-oxide (prepared according to the method of Y. Tamura et al., Heterocycles, 15:871-874 (1981)) is reacted with (S)-(-)-1-methyl-2-pyrrolidinemethanol according to the procedure of Example 3a, and the product is purified by chromatography on silica gel.

Workup

customthe product is purified by chromatography on silica gel

Sources & evidence

ORD record: ord-98d2684187894a2386ba0cd1a8fede10
Source dataset: uspto-grants-1999_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05914328

Reaction notes

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