p-Toluenesulfonic acid monohydrate → (2S)-2-[(benzylamino)methyl]-2,3,8,9-tetrahydro-7H-[1,4]dioxino[2,3-e]indol-8-one 4-methylbenzenesulfonate

HRID 1259464Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1259464
[CH2:1]([NH:8][CH2:9][C@H:10]1[CH2:15][O:14][C:13]2[CH:16]=[CH:17][C:18]([N+:24]([O-])=O)=[C:19]([CH2:20][C:21](O)=[O:22])[C:12]=2[O:11]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O.[C:28]1([CH3:38])[CH:33]=[CH:32][C:31]([S:34]([OH:37])(=[O:36])=[O:35])=[CH:30][CH:29]=1>[Pt].CO>[CH3:38][C:28]1[CH:29]=[CH:30][C:31]([S:34]([OH:37])(=[O:36])=[O:35])=[CH:32][CH:33]=1.[CH2:1]([NH:8][CH2:9][C@@H:10]1[O:11][C:12]2=[C:19]3[C:18](=[CH:17][CH:16]=[C:13]2[O:14][CH2:15]1)[NH:24][C:21](=[O:22])[CH2:20]3)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

5

Edukt 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 59456457{(3S)-3-[(benzylamino)methyl]-6-nitro-2,3-dihydro-1,4-benzodioxin-5-yl}acetic acid

Produkt 1

HCID 86644796(2S)-2-[(benzylamino)methyl]-2,3,8,9-tetrahydro-7H-[1,4]dioxino[2,3-e]indol-8-one 4-methylbenzenesulfonateAusbeute 61,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23939PlatinumKatalysatorHCID 887MethanolLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

A 50 mL two necked flask equipped with a magnetic stir bar, gas inlet adapter and gas outlet adapter is charged with {(3S)-3-[(benzylamino)methyl]-6-nitro-2,3-dihydro-1,4-benzodioxin-5-yl}acetic acid [from above (1.36 g, 3.80 mmol)], methanol (20 mL), and p-toluenesulfonic acid monohydrate (1.80 g, 9.5 mmol) and platinum (5% on carbon, 62% w/w water, 0.27 g). The flask head space is flushed with hydrogen gas (100 mL), the gas outlet adapter is closed and the slurry is stirred under a hydrogen atmosphere for 18 h under hydrogen, at which point the reaction is complete by LCMS. The catalyst is removed by vacuum filtration, and the resulting solution is heated to 50° C. (external) in an oil bath for 48 h. The solids are collected by vacuum filtration, the filter cake is washed with cold MeOH (10 mL) and dried under nitrogen giving (2S)-2-[(benzylamino)methyl]-2,3,8,9-tetrahydro-7H-[1,4]dioxino[2,3-e]indol-8-one 4-methylbenzenesulfonate (1.12 g, 61%) as an off-white powder.

Aufarbeitung

  1. customThe flask head space is flushed with hydrogen gas (100 mL)
  2. customthe gas outlet adapter is closed
  3. customThe catalyst is removed by vacuum filtration
  4. filtrationThe solids are collected by vacuum filtration
  5. washthe filter cake is washed with cold MeOH (10 mL)
  6. customdried under nitrogen

Quellen und Nachweise

ORD-Eintrag
ord-da48047a775f4411a0525c22fd24edaf
Quelldatensatz
uspto-grants-2013_06
Patentnummer
US08466296B2

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