Sodium hydride → tert-butyl-4-[(1R,2R)-2-({[4-(methylsulfonyl)benzyl]oxy}methyl)cyclopropyl]piperidine-1-carboxylate

HRID 1468824

반응식

HRID 1468824 반응식
[CH3:1][S:2]([C:5]1[CH:12]=[CH:11][C:8]([CH2:9][OH:10])=[CH:7][CH:6]=1)(=[O:4])=[O:3].[H-].[Na+].[C:15]([O:19][C:20]([N:22]1[CH2:27][CH2:26][CH:25]([C@H:28]2[CH2:30][C@H:29]2[CH2:31]I)[CH2:24][CH2:23]1)=[O:21])([CH3:18])([CH3:17])[CH3:16]>CN(C=O)C>[C:15]([O:19][C:20]([N:22]1[CH2:23][CH2:24][CH:25]([C@H:28]2[CH2:30][C@H:29]2[CH2:31][O:10][CH2:9][C:8]2[CH:11]=[CH:12][C:5]([S:2]([CH3:1])(=[O:3])=[O:4])=[CH:6][CH:7]=2)[CH2:26][CH2:27]1)=[O:21])([CH3:18])([CH3:16])[CH3:17]

참가 물질

5

반응물 3

HCID 24758Sodium hydrideHCID 3801026(4-Methanesulfonylphenyl)methanolHCID 86717780tert-butyl-4-[(1R,2R)-2-(iodomethyl)cyclopropyl]piperidine-1-carboxylate

생성물 1

HCID 86717779tert-butyl-4-[(1R,2R)-2-({[4-(methylsulfonyl)benzyl]oxy}methyl)cyclopropyl]piperidine-1-carboxylate

시약·촉매·용매 1

HCID 6228Dimethylformamide용매2회

실험 절차

4-(Methylsulfonyl)benzyl alcohol (1.0 g, 5.4 mmol) was dissolved in DMF (12 mL), and sodium hydride (60 wt % dispersion in oil, 320 mg, 8 mmol) was added. The iodide from step A (2.35 g, 6.4 mmol) in DMF (12 mL) was added and the resulting solution was stirred at RT for 15 h. The solution was quenched with sat. NH4Cl, and EtOAc. The organic layer was washed with water and brine. The organic layer was dried over Na2SO4, filtered, and concentrated. The residue was purified via silica gel column chromatography (2/1 hexanes/EtOAc) which provided the title compound.

후처리

  1. customThe solution was quenched with sat. NH4Cl, and EtOAc
  2. washThe organic layer was washed with water and brine
  3. dry with materialThe organic layer was dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified via silica gel column chromatography (2/1 hexanes/EtOAc) which

출처 및 근거

ORD 기록
ord-8939a06517de45dd9a4270bc99e806fb
출처 데이터셋
uspto-grants-2015_04
특허 번호
US09006228B2

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