Sulfuric acid magnesium salt (1:1) → Tert-butyl 3-ethyl-1-oxo-2,8-diazaspiro[4.5]decane-8-carboxylate

HRID 1501809노트

반응식

HRID 1501809 반응식
O=[C:2]([CH2:22][CH3:23])[CH2:3][C:4]1([C:17](OCC)=[O:18])[CH2:9][CH2:8][N:7]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:6][CH2:5]1.C([O-])(=O)C.[NH4+].C([BH3-])#[N:30].[Na+].S([O-])([O-])(=O)=O.[Mg+2]>C(O)C>[CH2:22]([CH:2]1[CH2:3][C:4]2([CH2:9][CH2:8][N:7]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:6][CH2:5]2)[C:17](=[O:18])[NH:30]1)[CH3:23]

참가 물질

6

반응물 4

HCID 24083Sulfuric acid magnesium salt (1:1)HCID 517165Ammonium AcetateHCID 5003444Sodium cyanoborohydrideHCID 867095041-Tert-butyl 4-ethyl 4-(2-oxobutyl)piperidine-1,4-dicarboxylate

생성물 1

HCID 86709505Tert-butyl 3-ethyl-1-oxo-2,8-diazaspiro[4.5]decane-8-carboxylate

시약·촉매·용매 1

HCID 702Ethanol용매

반응 조건

온도
80 °C

실험 절차

To a stirred solution of 1-tert-butyl 4-ethyl 4-(2-oxobutyl)piperidine-1,4-dicarboxylate (0.78 g, 2.38 mmol) in ethanol (24 mL) in a sealed tube was added ammonium acetate (2.39 g, 31.0 mmol), sodium cyanoborohydride (0.422 g, 6.72 mmol) and magnesium sulfate (1.577 g, 13.10 mmol) and the resulting mixture was heated for 16 hours at 80° C. The reaction mixture was filtered over CELITE® to remove MgSO4 and the filtrate was concentrated. The residue was re-dissolved in DCM (20 mL) and washed with saturated NaHCO3 (10 ml), water (10 mL) and brine (10 mL). The organic layer was dried over anhydrous MgSO4 filtered, concentrated, then purified by silica gel column chromatography (40 g RediSep Gold column) using (0-10) % MeOH/EtOAc to give the title compound.

후처리

  1. filtrationThe reaction mixture was filtered over CELITE®
  2. customto remove MgSO4
  3. concentrationthe filtrate was concentrated
  4. dissolutionThe residue was re-dissolved in DCM (20 mL)
  5. washwashed with saturated NaHCO3 (10 ml), water (10 mL) and brine (10 mL)
  6. dry with materialThe organic layer was dried over anhydrous MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. custompurified by silica gel column chromatography (40 g RediSep Gold column)

출처 및 근거

ORD 기록
ord-9147a3852bf74f01a14e48cedb440fe0
출처 데이터셋
uspto-grants-2015_12
특허 번호
US09206198B2

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