Acetate → 1,1,3-Trimethylindan-4-amine

HRID 2369

Reaktionsgleichung

Reaktionsgleichung von HRID 2369
C([O-])(=O)C.C(OC(C)C([N:12]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH:15]([CH3:22])[CH2:14][C:13]1([CH3:24])[CH3:23])=O)(=O)C.OS(O)(=O)=O.N>C(O)(=O)C.O>[NH2:12][C:21]1[CH:20]=[CH:19][CH:18]=[C:17]2[C:16]=1[CH:15]([CH3:22])[CH2:14][C:13]2([CH3:23])[CH3:24]

Komponenten

7

Edukt 4

HCID 175AcetateHCID 222AmmoniaHCID 1118Sulfuric AcidHCID 196903281-(2-Acetoxypropionyl)-1,2,3,4-tetrahydro-2,2,4-trimethylquinoline

Produkt 1

HCID 112175411,1,3-Trimethylindan-4-amineAusbeute 75 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 176Acetic AcidLösungsmittelHCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

The acetate compound prepared in B (ii) (55 g, GC purity 91%, 0.172 moles) was added over 45 minutes to 98% H2SO4 (50 ml) at 25°-60° C. (exotherm). After stirring for a further 30 minutes at 60° C., water (50 ml) containing acetic acid (10 ml) was cautiously added dropwise and the mixture heated at 100° C. for 3 hours. Petrol (60/80 b.p., 100 ml) was added and the mixture basified to pH 9 with 35% aqueous ammonia (150 ml). Separation of the organic layer, drying (MgSO4) and solvent flash gave the desired product (22.6 g, GC purity 92%, yield 69%). NMR analysis using chiral solvating agent [(-)-2,2,2-trifluoro-1-(9-anthryl)ethanol] showed a 70/30 mixture of enantiomers in favour of the (-)-isomer.

Aufarbeitung

  1. additionwas cautiously added dropwise
  2. temperaturethe mixture heated at 100° C. for 3 hours
  3. customSeparation of the organic layer
  4. dry with materialdrying (MgSO4) and solvent flash

Quellen und Nachweise

ORD-Eintrag
ord-d7d6fec5e6d54cc5b295691760de5f99
Quelldatensatz
uspto-grants-1998_03
Patentnummer
US05728869

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