Tetrahydrofuran → 1-(2-Tributylstannylmethoxyethyl)piperidine

HRID 642955노트

반응식

HRID 642955 반응식
[N:1]1([CH2:7]O)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[O:9]1CCC[CH2:10]1.[H-].[Na+].[CH2:16]([Sn:20]([CH2:27][CH2:28][CH2:29][CH3:30])([CH2:23][CH2:24][CH2:25][CH3:26])[CH2:21]I)[CH2:17][CH2:18][CH3:19]>C(OCC)(=O)C.O.CN(C)C=O>[CH2:16]([Sn:20]([CH2:21][O:9][CH2:10][CH2:7][N:1]1[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1)([CH2:27][CH2:28][CH2:29][CH3:30])[CH2:23][CH2:24][CH2:25][CH3:26])[CH2:17][CH2:18][CH3:19]

참가 물질

8

반응물 4

HCID 8028Tetrahydrofuran2회HCID 24758Sodium hydrideHCID 446909Piperidin-1-ylmethanolHCID 10862926Tributyl(iodomethyl)stannane

생성물 1

HCID 592597131-(2-Tributylstannylmethoxyethyl)piperidine수율 70%

시약·촉매·용매 3

HCID 962Water용매HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

실험 절차

To a mixture of 1-piperidinemethanol (1.3 g, 10 mmol) and tetrahydrofuran (30 ml) was added sodium hydride (60%, 418 mg, 10 mmol) at 0° C. (external temperature), followed by stirring at room temperature for 30 minutes. Then, to the reaction mixture was added dropwise a mixture of tributyl-iodomethyl-tin (3.0 g, 7.0 mmol), tetrahydrofuran (5 ml), and N,N-dimethylformamide (30 ml) at 0° C. Then, the reaction mixture was stirred at room temperature for 1 hour. To the reaction mixture were added water and ethyl acetate, and the organic layer was separated. The organic layer was sequentially washed with water and an aqueous saturated sodium chloride solution, and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (heptane:ethyl acetate=20:1, NH silica gel) to obtain the title compound (2.1 g, 4.9 mmol, 70%).

후처리

  1. additionThen, to the reaction mixture was added dropwise
  2. stirringThen, the reaction mixture was stirred at room temperature for 1 hour
  3. customthe organic layer was separated
  4. washThe organic layer was sequentially washed with water
  5. dry with materialan aqueous saturated sodium chloride solution, and dried over anhydrous magnesium sulfate
  6. distillationThe solvent was distilled off under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (heptane:ethyl acetate=20:1, NH silica gel)

출처 및 근거

ORD 기록
ord-5ab49a22196246278e41eb1f3ddff58e
출처 데이터셋
uspto-grants-2010_04
특허 번호
US07696347B2

반응 노트

불러오는 중…