Hydrogen Peroxide → HCID 23372103, compound

HRID 1708624Notes

Reaction equation

[CH2:1]([O:4][CH:5]1[CH2:10][C:9]([CH3:12])([CH3:11])[N:8]([O:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])[C:7]([CH3:23])([CH3:22])[CH2:6]1)[CH:2]=[CH2:3].C12BC(CCC1)CCC2.[OH-:33].[Na+].OO>O1CCCC1.O.CCOCC>[CH2:14]([O:13][N:8]1[C:7]([CH3:22])([CH3:23])[CH2:6][CH:5]([O:4][CH2:1][CH2:2][CH2:3][OH:33])[CH2:10][C:9]1([CH3:11])[CH3:12])[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21]

Participants

Conditions

Temperature: 20 °C

Procedure

A solution of 14.9 grams (45.9 mmol) of 4-allyloxy-1-octyloxy-2,2,6,6-tetramethylpiperidine (prepared in Example 10A) in 20 ml of anhydrous tetrahydrofuran is added over a 10-minute period to a solution of 5.6 grams (45.9 mmol) of 9-borabicyclo [3.3.1]nonane in 20 ml of tetrahydrofuran under a nitrogen atmosphere. The reaction mixture is cooled to 20° C. and a solution of 1.84 gram (45.9 mmol) of sodium hydroxide in water is added over a 10-minute period. A solution of 15.3 ml of 30% aqueous hydrogen peroxide is then added over 30 minutes while the reaction mixture is cooled in an ice-water bath. The reaction mixture is diluted with ether (50 ml) and the organic layer is separated and dried over potassium carbonate. Solvent is evaporated and the residue is purified by flash chromatography (silica gel; 2:1 heptane: ethyl acetate) to afford 14.0 grams (89 % yield) of the title compound is a colorless syrup.

Workup

temperatureis cooled in an ice-water bath
customthe organic layer is separated
dry with materialdried over potassium carbonate
customSolvent is evaporated
customthe residue is purified by flash chromatography (silica gel; 2:1 heptane: ethyl acetate)

Sources & evidence

ORD record: ord-deed29829bd3431e933c4ac17d3175a8
Source dataset: uspto-grants-1994_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05359069

Reaction notes

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