Toluene → Tert-butyl 4-(2-oxo-2-(piperidin-1-yl)ethoxy)piperidine-1-carboxylate

HRID 1091791노트

반응식

HRID 1091791 반응식
[OH:1][CH:2]1[CH2:7][CH2:6][N:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:4][CH2:3]1.Cl[CH2:16][C:17]([N:19]1[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]1)=[O:18].C1(C)C=CC=CC=1.[OH-].[Na+]>S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC.O>[O:18]=[C:17]([N:19]1[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]1)[CH2:16][O:1][CH:2]1[CH2:3][CH2:4][N:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:6][CH2:7]1

참가 물질

7

반응물 4

HCID 1140TolueneHCID 14798Sodium HydroxideHCID 2223122-Chloro-1-piperidine-1-yl-ethanoneHCID 643502Tert-butyl 4-hydroxypiperidine-1-carboxylate

생성물 1

HCID 57791806Tert-butyl 4-(2-oxo-2-(piperidin-1-yl)ethoxy)piperidine-1-carboxylate수율 96.2%

시약·촉매·용매 2

HCID 94433Tetrabutylammonium hydrogen sulfate촉매HCID 962Water용매

반응 조건

온도
25 °C

실험 절차

Tert-butyl 4-hydroxypiperidine-1-carboxylate (10 g, 49.69 mmol), tetrabutylammonium hydrogensulfate (0.844 g, 2.48 mmol) and 2-chloro-1-(piperidin-1-yl)ethanone (8.08 g, 49.69 mmol) were added to toluene (75 mL) to this was added sodium hydroxide (49.7 g, 496.86 mmol) in water (20 ml) and the reaction was stirred at 25° C. overnight. The reaction mixture was quenched with water (100 mL), extracted with Et2O (3×75 mL), the organic layer was dried over MgSO4, filtered and evaporated to afford the crude product as an orange liquid (15.60 g, 96% yield); 1H NMR (400.132 MHz, CDCl3) δ 1.49 (9H, s), 1.51-1.60 (2H, m), 1.61-1.68 (2H, m), 1.81-1.90 (3H, m), 3.05-3.13 (2H, m), 3.35-3.47 (2H, m), 3.50-3.62 (4H, m), 3.71-3.79 (2H, m), 3.80-3.89 (2H, m), 4.13-4.19 (2H, m).

후처리

  1. customThe reaction mixture was quenched with water (100 mL)
  2. extractionextracted with Et2O (3×75 mL)
  3. dry with materialthe organic layer was dried over MgSO4
  4. filtrationfiltered
  5. customevaporated

출처 및 근거

ORD 기록
ord-4947c64ec8474161a75f37212a7a533f
출처 데이터셋
uspto-grants-2012_03
특허 번호
US08129380B2

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