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

HRID 1176275

반응식

HRID 1176275 반응식
[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

참가 물질

6

반응물 4

HCID 962WaterHCID 140751,3,2-Dioxathiolane, 2,2-dioxideHCID 24758Sodium hydrideHCID 45074240HCID 45074240, 화합물

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매2회

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-bf0ed10be5b14d4ba022f8272fe8eab4
출처 데이터셋
uspto-grants-2010_11
특허 번호
US07842688B2

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