Water → Tert-butyl 3-(2-hydroxyethoxy)-4-(4-methoxyphenyl)piperidine-1-carboxylate

HRID 1712305

反応式

HRID 1712305 の反応式
[OH:1][CH:2]1[CH:7]([C:8]2[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[CH:10][CH:9]=2)[CH2:6][CH2:5][N:4]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:3]1.[H-].[Na+].[O:25]1[CH2:29][CH2:28]OS1(=O)=O.O>CN(C)C=O>[OH:25][CH2:29][CH2:28][O:1][CH:2]1[CH:7]([C:8]2[CH:9]=[CH:10][C:11]([O:14][CH3:15])=[CH:12][CH:13]=2)[CH2:6][CH2:5][N:4]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:3]1

参加物

6

反応物 4

HCID 962WaterHCID 140751,3,2-Dioxathiolane, 2,2-dioxideHCID 24758Sodium hydrideHCID 45074240HCID 45074240、化合物

生成物 1

HCID 68501804Tert-butyl 3-(2-hydroxyethoxy)-4-(4-methoxyphenyl)piperidine-1-carboxylate

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒2 回

実験手順

A solution of 1.01 g of tert-butyl 3-hydroxy-4(4-methoxyphenyl)piperidine-1-carboxylate in 40 ml of N,N-dimethylformamide is added at 0° C. to the suspension of 0.26 g of sodium hydride dispersion (60%) in 40 ml of N,N-dimethylformamide. After 30 minutes, the reaction mixture is admixed with 0.83 g of [1,3,2]dioxathiolane 2,2-dioxide and stirred at room temperature over 18 hours. The reaction mixture is cooled to 0° C., admixed with water and concentrated by evaporation. The residue is stirred in a 1:10 mixture of 0.1 M H2SO4/dioxane at 50° C. over 60 hours, neutralized with saturated aqueous sodium hydrogencarbonate solution and concentrated by evaporation. The residue is dissolved in ethyl acetate, washed with water and brine, dried over sodium sulphate and concentrated by evaporation. The title compound is obtained as a yellow oil from the residue by means of flash chromatography (SiO2 60F). Rf=0.20 (1:1 EtOAc-heptane); Rt=4.24.

後処理

  1. temperatureThe reaction mixture is cooled to 0° C.
  2. concentrationconcentrated by evaporation
  3. stirringThe residue is stirred in a 1:10 mixture of 0.1 M H2SO4/dioxane at 50° C. over 60 hours
  4. concentrationconcentrated by evaporation
  5. dissolutionThe residue is dissolved in ethyl acetate
  6. washwashed with water and brine
  7. dry with materialdried over sodium sulphate
  8. concentrationconcentrated by evaporation

出典と根拠

ORDレコード
ord-2f9ad858c81241e88ad54b00f68ea783
出典データセット
uspto-grants-2010_09
特許番号
US07790715B2

関連ノート

読み込み中…