(1R,2R)-trans-N-Boc-1,2-cyclohexanediamine → tert-Butyl (1R,2R)-2-(1-(4-(oxazol-2-yl)phenyl)piperidin-3-ylamino)cyclohexylcarbamate

HRID 2369985Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2369985
CS(O[CH:6]1[CH2:11][CH2:10][CH2:9][N:8]([C:12]2[CH:17]=[CH:16][C:15]([C:18]3[O:19][CH:20]=[CH:21][N:22]=3)=[CH:14][CH:13]=2)[CH2:7]1)(=O)=O.[NH2:23][C@@H:24]1[CH2:29][CH2:28][CH2:27][CH2:26][C@H:25]1[NH:30][C:31](=[O:37])[O:32][C:33]([CH3:36])([CH3:35])[CH3:34]>C(#N)C>[O:19]1[CH:20]=[CH:21][N:22]=[C:18]1[C:15]1[CH:16]=[CH:17][C:12]([N:8]2[CH2:9][CH2:10][CH2:11][CH:6]([NH:23][C@@H:24]3[CH2:29][CH2:28][CH2:27][CH2:26][C@H:25]3[NH:30][C:31](=[O:37])[O:32][C:33]([CH3:35])([CH3:34])[CH3:36])[CH2:7]2)=[CH:13][CH:14]=1.[O:19]1[CH:20]=[CH:21][N:22]=[C:18]1[C:15]1[CH:14]=[CH:13][C:12]([N:8]2[CH2:9][CH2:10][CH2:11][CH:6]2[CH2:7][NH:23][C@@H:24]2[CH2:29][CH2:28][CH2:27][CH2:26][C@H:25]2[NH:30][C:31](=[O:37])[O:32][C:33]([CH3:35])([CH3:34])[CH3:36])=[CH:17][CH:16]=1

Komponenten

5

Edukt 2

HCID 1514390(1R,2R)-trans-N-Boc-1,2-cyclohexanediamineHCID 866902081-(4-(Oxazol-2-yl)phenyl)piperidin-3-yl methanesulfonate

Produkt 2

HCID 71233117tert-Butyl (1R,2R)-2-(1-(4-(oxazol-2-yl)phenyl)piperidin-3-ylamino)cyclohexylcarbamateHCID 86690209tert-butyl (1R,2R)-2-((1-(4-(oxazol-2-yl)phenyl)pyrrolidin-2-yl)methylamino)cyclohexylcarbamate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

To a solution of 1-(4-(oxazol-2-yl)phenyl)piperidin-3-yl methanesulfonate (110 mg, 0.341 mmol) in acetonitrile (4 mL) was added tert-butyl (1R,2R)-2-aminocyclohexylcarbamate (110 mg, 0.512 mmol). The reaction was stirred in a microwave at 120° C. for 30 min. After this time, LC/MS showed two pairs of products formed. The reaction was concentrated. The residue was diluted with EtOAc and washed with water. EtOAc extracts were concentrated. The resulting residue was purified using silica gel chromatography (ISCO system) eluting with a gradient of 50-100% EtOAc/Hex to give desired product tert-butyl (1R,2R)-2-((1-(4-(oxazol-2-yl)phenyl)pyrrolidin-2-yl)methylamino)cyclohexylcarbamate and the unwanted diastereomer, tert-butyl (1R,2S)-2-((1-(4-(oxazol-2-yl)phenyl)pyrrolidin-2-yl)methylamino)cyclohexylcarbamate (156 mg total) as a white foam.

Aufarbeitung

  1. customformed
  2. concentrationThe reaction was concentrated
  3. additionThe residue was diluted with EtOAc
  4. washwashed with water
  5. concentrationEtOAc extracts were concentrated
  6. customThe resulting residue was purified
  7. washeluting with a gradient of 50-100% EtOAc/Hex

Quellen und Nachweise

ORD-Eintrag
ord-bc1c982a2d2e4b53993fcc6b498a2c4d
Quelldatensatz
uspto-grants-2014_04
Patentnummer
US08710049B2

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