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

HRID 474280

Reaktionsgleichung

Reaktionsgleichung von HRID 474280
[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]

Komponenten

6

Edukt 3

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 30318Osmium TetroxideKatalysatorHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

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).

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-07fa7bbc91354d9d844b50e9146c33aa
Quelldatensatz
uspto-grants-2014_01
Patentnummer
US08637523B2

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