p-Toluenesulfonic acid → 8-t-Butyl-2-(4,6-dimethylpyrimid-2-ylaminomethyl)-1,4-dioxaspiro(4,5)decane

HRID 52398

Reaktionsgleichung

Reaktionsgleichung von HRID 52398
[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[N:5]=[C:4]([NH:9][CH2:10][CH:11]([OH:14])[CH2:12][OH:13])[N:3]=1.[C:15]([CH:19]1[CH2:24][CH2:23][C:22](=O)[CH2:21][CH2:20]1)([CH3:18])([CH3:17])[CH3:16].C1(C)C=CC(S(O)(=O)=O)=CC=1>C1C=CC=CC=1>[C:15]([CH:19]1[CH2:24][CH2:23][C:22]2([O:14][CH:11]([CH2:10][NH:9][C:4]3[N:5]=[C:6]([CH3:8])[CH:7]=[C:2]([CH3:1])[N:3]=3)[CH2:12][O:13]2)[CH2:21][CH2:20]1)([CH3:18])([CH3:17])[CH3:16]

Komponenten

5

Edukt 3

HCID 6101p-Toluenesulfonic acidHCID 73924-tert-ButylcyclohexanoneHCID 199636663-(4,6-Dimethylpyrimid-2-ylamino)propane-1,2-diol

Produkt 1

HCID 199636678-t-Butyl-2-(4,6-dimethylpyrimid-2-ylaminomethyl)-1,4-dioxaspiro(4,5)decaneAusbeute 90 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 241BenzeneLösungsmittel

Versuchsvorschrift

3-(4,6-dimethylpyrimid-2-ylamino)-propane-1,2-diol (4.0 g, 20 mmol), 4-t-butyl cyclohexanone (3.08 g, 20 mmol) and p-toluenesulfonic acid (4.3 g, 22 mmol) in 50 ml benzene were refluxed on a water trap for 1 hour. The reaction mixture was washed twice with saturated aqueous sodium carbonate (50 ml), dried with magnesium sulphate and evaporated in vacuum. Kugelrohr- distillation of the resulting oil yielded 6.0 g of a colourless oil (b.p. 200° C./0.2 mbar) which was recrystallised from light petroleum to yield 5.0 g of colourless crystals (m.p. 121°-124° C.). GLG-MS analysis indicates an approximately 1:1 mixture of diastereoisomers (cis/trans).

Aufarbeitung

  1. washThe reaction mixture was washed twice with saturated aqueous sodium carbonate (50 ml)
  2. dry with materialdried with magnesium sulphate
  3. customevaporated in vacuum
  4. distillationKugelrohr- distillation of the resulting oil

Quellen und Nachweise

ORD-Eintrag
ord-ea9d841dea47442f9ffde8a62db28f90
Quelldatensatz
uspto-grants-1997_04
Patentnummer
US05616708

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