Formic Acid → 4-{2-[Methyl(2-methyl-2-(methyldisulphanyl)propyl)amino]ethoxy)-2,6-bis(hydroxymethyl)pyridine

HRID 446641Notes

Reaction equation

[CH:1](O)=O.[CH3:4][C:5]([S:22][S:23][CH3:24])([CH3:21])[CH2:6][NH:7][CH2:8][CH2:9][O:10][C:11]1[CH:16]=[C:15]([CH2:17][OH:18])[N:14]=[C:13]([CH2:19][OH:20])[CH:12]=1.[OH-].[Na+]>C=O>[CH3:1][N:7]([CH2:6][C:5]([CH3:4])([S:22][S:23][CH3:24])[CH3:21])[CH2:8][CH2:9][O:10][C:11]1[CH:12]=[C:13]([CH2:19][OH:20])[N:14]=[C:15]([CH2:17][OH:18])[CH:16]=1

Participants

Conditions

Temperature: 100 °C

Procedure

365 μl of formic acid are added to a suspension, cooled to 0° C., of 322 mg of 4-[2-(2-methyl-2-(methyldisulphanyl)propylamino)ethoxy]-2,6-bis(hydroxymethyl)pyridine in 262 μl of formaldehyde. The mixture is heated at 100° C. for 1¼ hours. After returning to ambient temperature, the mixture is hydrolysed and then a 5N aqueous sodium hydroxide solution is added until a pH=12 is obtained. The aqueous phase is extracted 3× with AcOEt and the combined organic phases are dried over MgSO4 and concentrated under RP. 310 mg of 4-{2-[methyl(2-methyl-2-(methyldisulphanyl)propyl)amino]ethoxy}-2,6-bis(hydroxymethyl)pyridine are thus obtained.

Workup

customAfter returning to ambient temperature
customis obtained
extractionThe aqueous phase is extracted 3× with AcOEt
dry with materialthe combined organic phases are dried over MgSO4
concentrationconcentrated under RP

Sources & evidence

ORD record: ord-7fab5cd5e1dd4cb3a89b1f4d3d55c89b
Source dataset: uspto-grants-2013_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08481042B2

Reaction notes

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