Water → 2-(3,4-Dihydroxybutyl)isoindoline-1,3-dione

HRID 474280

反応式

HRID 474280 の反応式
[CH2:1]([N:5]1[C:13](=[O:14])[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6]1=[O:15])[CH2:2][CH:3]=[CH2:4].C[N+]1([O-])CC[O:20]CC1.[OH2:24]>C1COCC1.[Os](=O)(=O)(=O)=O>[OH:24][CH:3]([CH2:4][OH:20])[CH2:2][CH2:1][N:5]1[C:13](=[O:14])[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6]1=[O:15]

参加物

6

反応物 3

HCID 962WaterHCID 82029Methyl morpholine oxideHCID 339432N-(3-Buten-1-yl)phthalimide

生成物 1

HCID 215924892-(3,4-Dihydroxybutyl)isoindoline-1,3-dione

試薬・触媒・溶媒 2

HCID 30318Osmium Tetroxide触媒HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of 2-(but-3-enyl)isoindoline-1,3-dione (5.20 g, 25.8 mmol) in THF (86 mL) was added 4-methylmorpholine 4-oxide (4.54 g, 38.8 mmol) followed by osmium(VIII) oxide in water (3.16 mL, 0.517 mmol) dropwise. The reaction mixture was stirred at rt for 6 h. A saturated Na2S2SO3 solution was added to the reaction mixture and stirred for another 10 min. The aqueous layer was separated and extracted with EtOAc three times, and the combined organic layers were washed with water, brine and dried over Na2SO4. The solids were filtered off, and the filtrate was concentrated in vacuo to get 2-(3,4-dihydroxybutyl)isoindoline-1,3-dione which was used as-is in the next step. LC-MS (M+Na)+=258.1. 1H NMR (500 MHz, methanol-d4) δ 7.92-7.85 (m, 2H), 7.85-7.75 (m, 2H), 3.91-3.75 (m, 2H), 3.65 (dtd, J=9.1, 5.5, 3.7 Hz, 1H), 3.55-3.43 (m, 2H), 1.95-1.85 (m, 1H), 1.80-1.65 (m, 1H).

後処理

  1. stirringstirred for another 10 min
  2. customThe aqueous layer was separated
  3. extractionextracted with EtOAc three times
  4. washthe combined organic layers were washed with water, brine
  5. dry with materialdried over Na2SO4
  6. filtrationThe solids were filtered off
  7. concentrationthe filtrate was concentrated in vacuo

出典と根拠

ORDレコード
ord-07fa7bbc91354d9d844b50e9146c33aa
出典データセット
uspto-grants-2014_01
特許番号
US08637523B2

関連ノート

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