Sulfuric acid magnesium salt (1:1) → N-(1,4-dioxaspiro[4.5]dec-8-ylidene)-2-methylpropane-2-sulfinamide

HRID 410713노트

반응식

HRID 410713 반응식
[CH3:1][C:2]([S@@:5]([NH2:7])=[O:6])([CH3:4])[CH3:3].[O:8]1[C:12]2([CH2:17][CH2:16][C:15](=O)[CH2:14][CH2:13]2)[O:11][CH2:10][CH2:9]1.C(=O)(O)[O-].[Na+].S([O-])([O-])(=O)=O.[Mg+2]>O1CCCC1.[O-]CC.[Ti+4].[O-]CC.[O-]CC.[O-]CC.C(#N)C>[O:8]1[C:12]2([CH2:17][CH2:16][C:15](=[N:7][S:5]([C:2]([CH3:4])([CH3:3])[CH3:1])=[O:6])[CH2:14][CH2:13]2)[O:11][CH2:10][CH2:9]1

참가 물질

8

반응물 4

HCID 24083Sulfuric acid magnesium salt (1:1)HCID 516892Sodium BicarbonateHCID 5674151,4-Dioxaspiro[4.5]decan-8-oneHCID 11355477tert-Butylsulfinamide, (S)-(-)-

생성물 1

HCID 59733754N-(1,4-dioxaspiro[4.5]dec-8-ylidene)-2-methylpropane-2-sulfinamide수율 28.1%

시약·촉매·용매 3

HCID 76524Titanium tetraethoxide촉매HCID 6342Acetonitrile용매HCID 8028Tetrahydrofuran용매

실험 절차

To a stirred solution of (S)-(−)-2-methyl-2-propanesulfinamide (854 mg, 7 mmol) and 1,4-dioxaspiro[4,5]decan-8-one (1 g, 6.40 mmol) in tetrahydrofuran (13 mL) was added titanium(IV) ethoxide (5.11 mL, 16 mmol). The mixture was stirred for 4 h at room temperature, poured over stirring saturated aqueous sodium bicarbonate (10 mL) and acetonitrile (10 mL), and stirred for 20 minutes. Magnesium sulfate was added and the mixture was stirred for 20 minutes, filtered over celite and concentrated. The residue was purified by column chromatography on silica gel (10:90 to 70:30 ethyl acetate:hexanes gradient) to afford N-(1,4-dioxaspiro[4.5]dec-8-ylidene)-2-methylpropane-2-sulfinamide (466 mg, 1.8 mmol, 28% yield) as a white solid. MS ESI: [M+H]+ m/z 260.

후처리

  1. additionpoured
  2. stirringstirred for 20 minutes
  3. stirringthe mixture was stirred for 20 minutes
  4. filtrationfiltered over celite and
  5. concentrationconcentrated
  6. customThe residue was purified by column chromatography on silica gel (10:90 to 70:30 ethyl acetate:hexanes gradient)

출처 및 근거

ORD 기록
ord-cc3ca0060e9e46d9b0888a5883ad71e9
출처 데이터셋
uspto-grants-2014_06
특허 번호
US08759366B2

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