Dimethyl Sulfoxide → 1-Methoxy-2,2,6,6-tetramethyl-piperidin-4-ol

HRID 1492703Notes

Reaction equation

OO.[OH:3][CH:4]1[CH2:9][C:8]([CH3:11])([CH3:10])[N:7]([OH:12])[C:6]([CH3:14])([CH3:13])[CH2:5]1.[CH3:15]S(C)=O>C(Cl)Cl.O>[CH3:15][O:12][N:7]1[C:8]([CH3:10])([CH3:11])[CH2:9][CH:4]([OH:3])[CH2:5][C:6]1([CH3:14])[CH3:13]

Participants

Conditions

Temperature: 45 °C

Procedure

A solution of 9.0 g (79 mmol) of 30% aqueous hydrogen peroxide is added dropwise, under nitrogen, over a 10-minute period to a mixture of 10.0 g (58.1 mmol) of 4-hydroxy-1-oxyl-2,2,6,6-tetramethylpiperidine, 31.4 g (64.1 mmol) of ferric sulfate pentahydrate, and 200 ml of dimethyl sulfoxide at a temperature of 20° C. No temperature change is observed as the hydrogen peroxide solution is added. After the addition is complete, the reaction mixture is stirred for 10 minutes. Water (50 ml) is added, and the temperature increases to 45° C. The mixture is diluted with methylene chloride (200 ml) and water (50 ml), and the aqueous layer is extracted with methylene chloride (2×100 ml). The organic layers are concentrated at reduced pressure, and the crude product is purified by flash chromatography on silica gel (4:1 heptane/ethyl acetate) to afford 1.25 g (11% yield) of the title compound, mp 93°-94° C.

Workup

additionis added
additionAfter the addition
extractionthe aqueous layer is extracted with methylene chloride (2×100 ml)
concentrationThe organic layers are concentrated at reduced pressure
customthe crude product is purified by flash chromatography on silica gel (4:1 heptane/ethyl acetate)

Sources & evidence

ORD record: ord-11c4c664b7d64f2a993804063bb4ba56
Source dataset: uspto-grants-1994_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05374729

Reaction notes

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