Sodium Iodide → 1-(tert-Butoxycarbonyl)-3-[[2-(4-chlorophenyl)-4-methylthiazol-5-yl]methoxymethyl]piperidine

HRID 602139

반응식

HRID 602139 반응식
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH2:11][CH:10]([CH2:14][OH:15])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].Cl[CH2:19][C:20]1[S:24][C:23]([C:25]2[CH:30]=[CH:29][C:28]([Cl:31])=[CH:27][CH:26]=2)=[N:22][C:21]=1[CH3:32].[I-].[Na+]>O1CCCC1.C(OCC)(=O)C>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH2:11][CH:10]([CH2:14][O:15][CH2:19][C:20]2[S:24][C:23]([C:25]3[CH:30]=[CH:29][C:28]([Cl:31])=[CH:27][CH:26]=3)=[N:22][C:21]=2[CH3:32])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

참가 물질

7

반응물 4

HCID 5238Sodium IodideHCID 24758Sodium hydrideHCID 27636945-(Chloromethyl)-2-(4-chlorophenyl)-4-methyl-1,3-thiazoleHCID 2763851tert-Butyl 3-(hydroxymethyl)piperidine-1-carboxylate

생성물 1

HCID 575721911-(tert-Butoxycarbonyl)-3-[[2-(4-chlorophenyl)-4-methylthiazol-5-yl]methoxymethyl]piperidine수율 59%

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매2회HCID 8857Ethyl Acetate용매

실험 절차

1-(tert-Butoxycarbonyl)piperidin-3-ylmethanol (215 mg, 1.00 mmol) was dissolved in tetrahydrofuran (5 mL). While this solution was chilled in an ice bath, 60% sodium hydride in oil (44.0 mg, 1.10 mmol) was added and the mixture was stirred for 20 min. Subsequently, 5-chloromethyl-2-(4-chlorophenyl)-4-methylthiazole (258 mg, 1.00 mmol) in tetrahydrofuran (5 mL) and sodium iodide (15.0 mg, 0.100 mmol) were added. The mixture was stirred for 2 hours while chilled in an ice bath and was further stirred for 6 hours at room temperature. Subsequently, ethyl acetate was added and the mixture washed sequentially with 5% aqueous citric acid and brine, followed by drying over magnesium sulfate and evaporation of the solvent. Purification of the resulting residue by silica gel column chromatography (hexane:ethyl acetate=20:1->5:1) gave 258 mg (59%) of the desired compound as a colorless oil.

후처리

  1. temperatureWhile this solution was chilled in an ice bath
  2. stirringThe mixture was stirred for 2 hours
  3. temperaturewhile chilled in an ice bath
  4. stirringwas further stirred for 6 hours at room temperature
  5. washthe mixture washed sequentially with 5% aqueous citric acid and brine
  6. dry with materialby drying over magnesium sulfate and evaporation of the solvent
  7. customPurification of the resulting residue by silica gel column chromatography (hexane:ethyl acetate=20:1->5:1)

출처 및 근거

ORD 기록
ord-44ea08233e7f437aa7b6be6eb59702be
출처 데이터셋
uspto-grants-2011_03
특허 번호
US07902367B2

연결된 노트

불러오는 중…