Trifluoroacetic acid → 1,1-Dimethylpropyl 4-[2-(4-methanesulfonylphenoxymethyl)pyridin-5-yl]piperidine-1-carboxylate

HRID 42154

반응식

HRID 42154 반응식
[CH3:1][S:2]([C:5]1[CH:31]=[CH:30][C:8]([O:9][CH2:10][C:11]2[CH:16]=[CH:15][C:14]([CH:17]3[CH2:22][CH2:21][N:20]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:19][CH2:18]3)=[CH:13][N:12]=2)=[CH:7][CH:6]=1)(=[O:4])=[O:3].F[C:33](F)(F)C(O)=O.C(N(CC)CC)C.C(OC(OC(CC)(C)C)=O)(OC(CC)(C)C)=O>ClCCl.O1CCCC1.O>[CH3:1][S:2]([C:5]1[CH:6]=[CH:7][C:8]([O:9][CH2:10][C:11]2[CH:16]=[CH:15][C:14]([CH:17]3[CH2:18][CH2:19][N:20]([C:23]([O:25][C:26]([CH3:28])([CH3:27])[CH2:29][CH3:33])=[O:24])[CH2:21][CH2:22]3)=[CH:13][N:12]=2)=[CH:30][CH:31]=1)(=[O:3])=[O:4]

참가 물질

8

반응물 4

HCID 6422Trifluoroacetic acidHCID 8471TriethylamineHCID 45860571,3-Bis(1,1-dimethylpropyl) dicarbonateHCID 44819975Tert-butyl 4-[2-(4-methanesulfonyl-phenoxymethyl)pyridin-5-yl]piperidine-1-carboxylate

생성물 1

HCID 670831001,1-Dimethylpropyl 4-[2-(4-methanesulfonylphenoxymethyl)pyridin-5-yl]piperidine-1-carboxylate수율 91%

시약·촉매·용매 3

HCID 962Water용매HCID 6344Dichloromethane용매HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of tert-butyl 4-[2-(4-methanesulfonyl-phenoxymethyl)pyridin-5-yl]piperidine-1-carboxylate (Example 1) (30 mg, 0.067 mmol) in dry dichloromethane (0.35 mL) under N2 was added trifluoroacetic acid (0.35 mL). The mixture was stirred at room temperature for 2 hours and concentrated in vacuo. To a solution of the residue in dry tetrahydrofuran (0.7 mL) was added triethylamine (28 μL, 0.2 mmol) and di-tert-amyl dicarbonate (25 μL, 0.1 mmol). The mixture was stirred at room temperature for 3 hours, diluted with water (1 mL) and extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=1/1) to give the title compound as a white crystal (28 mg, yield 91%).

후처리

  1. concentrationconcentrated in vacuo
  2. stirringThe mixture was stirred at room temperature for 3 hours
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=1/1)

출처 및 근거

ORD 기록
ord-7d0ab0edde834763a1aef8955ad7aca6
출처 데이터셋
uspto-grants-2013_09
특허 번호
US08536176B2

연결된 노트

불러오는 중…