Trimethylsilyl isocyanate → 4-(t-Butoxycarbonylamino)-1-(1-carbamoyl-4-piperidinylmethyl)piperidine

HRID 1597310

Reaktionsgleichung

Reaktionsgleichung von HRID 1597310
[C:1]([O:5][C:6]([NH:8][CH:9]1[CH2:14][CH2:13][N:12]([CH2:15][CH:16]2[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]2)[CH2:11][CH2:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C[Si]([N:26]=[C:27]=[O:28])(C)C>C(Cl)Cl>[C:1]([O:5][C:6]([NH:8][CH:9]1[CH2:10][CH2:11][N:12]([CH2:15][CH:16]2[CH2:17][CH2:18][N:19]([C:27](=[O:28])[NH2:26])[CH2:20][CH2:21]2)[CH2:13][CH2:14]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Komponenten

4

Edukt 2

HCID 70696Trimethylsilyl isocyanateHCID 129861544-(t-Butoxycarbonylamino)-1-(4-piperidinylmethyl)piperidine

Produkt 1

HCID 698309374-(t-Butoxycarbonylamino)-1-(1-carbamoyl-4-piperidinylmethyl)piperidineAusbeute 83,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of 4-(t-butoxycarbonylamino)-1-(4-piperidinylmethyl)piperidine (590 mg) in methylene chloride (30 ml) is added trimethylsilyl isocyanate (220 mg) under ice-cooling, and the mixture is stirred at room temperature for 8 hours. The reaction mixture is washed with water and a saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, and the solvent is evaporated under reduced pressure. The residue is purified by silica gel column chromatography (eluent; chloroform:methanol=10:1) to give 4-(t-butoxycarbonylamino)-1-(1-carbamoyl-4-piperidinylmethyl)piperidine (540 mg).

Aufarbeitung

  1. temperaturecooling
  2. washThe reaction mixture is washed with water
  3. dry with materiala saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate
  4. customthe solvent is evaporated under reduced pressure
  5. customThe residue is purified by silica gel column chromatography (eluent; chloroform:methanol=10:1)

Quellen und Nachweise

ORD-Eintrag
ord-2324d1ff461043089d5299707662b91e
Quelldatensatz
uspto-grants-2001_09
Patentnummer
US06294555B1

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