Benzyl Alcohol → Benzyl[2,2-dimethyl-5-(pyridin-3-yl)-1,3-dioxan-5-yl]carbamate

HRID 64445Notes

Reaction equation

[CH3:1][C:2]1([CH3:17])[O:7][CH2:6][C:5]([C:11]2[CH:12]=[N:13][CH:14]=[CH:15][CH:16]=2)(C(O)=O)[CH2:4][O:3]1.[CH2:18]([OH:25])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.C1(P([N:40]=[N+]=[N-])(C2C=CC=CC=2)=O)C=CC=CC=1.[C:43](=[O:46])([O-])O.[Na+]>C(OCC)(=O)C.C(N(CC)CC)C.C1(C)C=CC=CC=1>[CH2:18]([O:25][C:43](=[O:46])[NH:40][C:5]1([C:11]2[CH:12]=[N:13][CH:14]=[CH:15][CH:16]=2)[CH2:4][O:3][C:2]([CH3:1])([CH3:17])[O:7][CH2:6]1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

Conditions

Temperature: 100 °C

Procedure

To 1.09 g of 2,2-dimethyl-5-(pyridin-3-yl)-1,3-dioxane-5-carboxylic acid were added 20 ml of toluene, 0.9 ml of triethylamine, 2.4 ml of benzyl alcohol, and 1.3 ml of diphenylphosphoryl azide, followed by stirring at 100° C. for 17 hours. After leaving to be cooled, to the reaction mixture were added a saturated aqueous sodium hydrogen carbonate solution and ethyl acetate to carry out a layer separation operation. The organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography to obtain 1.01 g of benzyl[2,2-dimethyl-5-(pyridin-3-yl)-1,3-dioxan-5-yl]carbamate.

Workup

customAfter leaving
temperatureto be cooled, to the reaction mixture
customa layer separation operation
washThe organic layer was washed with saturated brine
dry with materialdried over anhydrous magnesium sulfate
customthe solvent was evaporated under reduced pressure
customThe obtained residue was purified by silica gel column chromatography

Sources & evidence

ORD record: ord-fe6a8b4c99004640842e478e34fded6d
Source dataset: uspto-grants-2016_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09447090B2

Reaction notes

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