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

HRID 410713ノート

反応式

HRID 410713 の反応式
[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

参加物

8

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 76524Titanium tetraethoxide触媒HCID 6342Acetonitrile溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-cc3ca0060e9e46d9b0888a5883ad71e9
出典データセット
uspto-grants-2014_06
特許番号
US08759366B2

反応ノート

読み込み中…