Potassium Carbonate → (2S)-3-cyclohexyl-2-{[2-(1-cyclohexyl-3,4-dihydroisoquinolin-2(1H)-yl)-2-oxoethyl]amino}propan-1-ol

HRID 2383074Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2383074
Cl[CH2:2][C:3]([N:5]1[CH2:14][CH2:13][C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH:6]1[CH:15]1[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]1)=[O:4].C(=O)([O-])[O-].[K+].[K+].Cl.[NH2:28][C@@H:29]([CH2:32][CH:33]1[CH2:38][CH2:37][CH2:36][CH2:35][CH2:34]1)[CH2:30][OH:31].[Cl-].[NH4+]>C(#N)C>[CH:33]1([CH2:32][C@H:29]([NH:28][CH2:2][C:3]([N:5]2[CH2:14][CH2:13][C:12]3[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=3)[CH:6]2[CH:15]2[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]2)=[O:4])[CH2:30][OH:31])[CH2:38][CH2:37][CH2:36][CH2:35][CH2:34]1

Komponenten

6

Edukt 4

HCID 11430Potassium CarbonateHCID 25517Ammonium ChlorideHCID 16212813(2S)-2-amino-3-cyclohexylpropan-1-ol hydrochlorideHCID 675372192-(Chloroacetyl)-1-cyclohexyl-1,2,3,4-tetrahydroisoquinoline

Produkt 1

HCID 59396522(2S)-3-cyclohexyl-2-{[2-(1-cyclohexyl-3,4-dihydroisoquinolin-2(1H)-yl)-2-oxoethyl]amino}propan-1-olAusbeute 24,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

To a solution of 2-(chloroacetyl)-1-cyclohexyl-1,2,3,4-tetrahydroisoquinoline (12 mg) in acetonitrile (0.5 mL) were added potassium carbonate (3 mg) and (S)-(+)-2-amino-3-cyclohexyl-1-propanol hydrochloride (15 mg), followed by stirring at 80° C. for 4 hours. Thereafter, a saturated aqueous ammonium chloride solution was added to the reaction liquid, followed by extraction with chloroform. The solvent was evaporated and the resulting residue was purified by preparative HPLC to obtain (2S)-3-cyclohexyl-2-{[2-(1-cyclohexyl-3,4-dihydroisoquinolin-2(1H)-yl)-2-oxoethyl]amino}propan-1-ol (4.1 mg).

Aufarbeitung

  1. extractionfollowed by extraction with chloroform
  2. customThe solvent was evaporated
  3. customthe resulting residue was purified by preparative HPLC

Quellen und Nachweise

ORD-Eintrag
ord-310254a4ff5a409fafc0cbb4379920d4
Quelldatensatz
uspto-grants-2012_09
Patentnummer
US08263607B2

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