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Imidazole → [4-(tert-Butyl-diphenyl-silanyloxy)-piperidin-1-yl]-acetic acid methyl ester

HRID 1670827
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HRID 1670827 반응식
[CH3:1][O:2][C:3](=[O:12])[CH2:4][N:5]1[CH2:10][CH2:9][CH:8]([OH:11])[CH2:7][CH2:6]1.N1C=CN=C1.[Si:18](Cl)([C:31]([CH3:34])([CH3:33])[CH3:32])([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.C(OCC)C>CN(C=O)C>[CH3:1][O:2][C:3](=[O:12])[CH2:4][N:5]1[CH2:10][CH2:9][CH:8]([O:11][Si:18]([C:31]([CH3:34])([CH3:33])[CH3:32])([C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=2)[C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH2:7][CH2:6]1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 4

HCID 795ImidazoleHCID 3283Diethyl EtherHCID 94078tert-ButyldiphenylchlorosilaneHCID 28837753Methyl 2-(4-hydroxypiperidin-1-yl)acetate

생성물 1

HCID 67354799[4-(tert-Butyl-diphenyl-silanyloxy)-piperidin-1-yl]-acetic acid methyl ester수율 73.2%

시약·촉매·용매 1

HCID 6228
Dimethylformamide
용매

실험 절차

Treat a solution of (4-hydroxy-piperidin-1-yl)-acetic acid methyl ester (10.0 g, 57.7 mmol) and imidazole (4.71 g, 69.2 mmol) in DMF (100 mL) with t-butyl-diphenylsilyl chloride (19.04 g, 69.3 mmol) and stir for 16 hours at room temperature. Dilute the reaction with diethyl ether and wash with water. Dry the organic layer (Na2SO4), remove the solvent in vacuo to afford crude product, and purify with a 2% methanol in CH2Cl2 to afford 17.38 g (73%) of the titled product. Rf=0.71 (9/1 CH2Cl2/methanol). ES MS (m/z): 412 (M+).

후처리

  1. additionDilute
  2. washwash with water
  3. dry with materialDry the organic layer (Na2SO4)
  4. customremove the solvent in vacuo
  5. customto afford crude product
  6. custompurify with a 2% methanol in CH2Cl2

출처 및 근거

ORD 기록
ord-ebf8026e3f0749868a1c83c7fe7b5cfd
출처 데이터셋
uspto-grants-2011_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07994176B2

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