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

HRID 64445ノート

反応式

HRID 64445 の反応式
[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

参加物

8

反応物 4

HCID 244Benzyl AlcoholHCID 199401P,P-Diphenylphosphinic azideHCID 516892Sodium BicarbonateHCID 900723352,2-Dimethyl-5-(pyridin-3-yl)-1,3-dioxane-5-carboxylic acid

生成物 1

HCID 131737220Benzyl[2,2-dimethyl-5-(pyridin-3-yl)-1,3-dioxan-5-yl]carbamate

試薬・触媒・溶媒 3

HCID 1140Toluene溶媒HCID 8471Triethylamine溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
100 °C

実験手順

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.

後処理

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

出典と根拠

ORDレコード
ord-fe6a8b4c99004640842e478e34fded6d
出典データセット
uspto-grants-2016_09
特許番号
US09447090B2

反応ノート

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