Hydrochloric Acid → tert-butyl (2S)-2-[(1-cyclohexyl-3,4-dihydroisoquinolin-2(1H)-yl)carbonyl]pyrrolidine-1-carboxylate

HRID 2383016Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2383016
CN1CCOCC1.[C:8]([O:12][C:13]([N:15]1[CH2:22][CH2:21][CH2:20][C@H:16]1[C:17]([OH:19])=O)=[O:14])([CH3:11])([CH3:10])[CH3:9].C(Cl)(=O)C(C)(C)C.Cl.[CH:31]1([CH:37]2[C:46]3[C:41](=[CH:42][CH:43]=[CH:44][CH:45]=3)[CH2:40][CH2:39][NH:38]2)[CH2:36][CH2:35][CH2:34][CH2:33][CH2:32]1.Cl>ClCCCl.CCOC(C)=O>[CH:31]1([CH:37]2[C:46]3[C:41](=[CH:42][CH:43]=[CH:44][CH:45]=3)[CH2:40][CH2:39][N:38]2[C:17]([C@@H:16]2[CH2:20][CH2:21][CH2:22][N:15]2[C:13]([O:12][C:8]([CH3:9])([CH3:10])[CH3:11])=[O:14])=[O:19])[CH2:32][CH2:33][CH2:34][CH2:35][CH2:36]1

Komponenten

8

Edukt 5

HCID 313Hydrochloric AcidHCID 79724-Methylmorpholine2×HCID 62493Pivaloyl chlorideHCID 850831,2-Pyrrolidinedicarboxylic acid, 1-(1,1-dimethylethyl) ester, (2S)-HCID 675358401-Cyclohexyl-1,2,3,4-tetrahydroisoquinoline hydrochloride

Produkt 1

HCID 68250501tert-butyl (2S)-2-[(1-cyclohexyl-3,4-dihydroisoquinolin-2(1H)-yl)carbonyl]pyrrolidine-1-carboxylateAusbeute 109,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 111,2-DichloroethaneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

N-methylmorpholine (0.873 mL) was added to a solution of 1-(tert-butoxycarbonyl)-L-proline (1.28 g) in 1,2-dichloroethane (10 mL) under ice-cooling, followed by further addition of pivaloyl chloride (0.734 mL). The reaction liquid was stirred for 1 hour, and N-methylmorpholine (1.09 mL) and 1-cyclohexyl-1,2,3,4-tetrahydroisoquinoline hydrochloride (1.00 g) were then added thereto. The mixture was stirred at room temperature for 15 hours. To the reaction solution were added EtOAc and an aqueous 1 M HCl solution. The organic layer was washed with water, a saturated aqueous sodium hydrogen carbonate solution, and saturated brine, dried over magnesium sulfate, and filtered. The filtrate was concentrated under reduced pressure to obtain tert-butyl (2S)-2-[(1-cyclohexyl-3,4-dihydroisoquinolin-2(1H)-yl)carbonyl]pyrrolidine-1-carboxylate (1.79 g).

Aufarbeitung

  1. temperaturecooling
  2. customThe reaction liquid
  3. stirringThe mixture was stirred at room temperature for 15 hours
  4. washThe organic layer was washed with water
  5. dry with materiala saturated aqueous sodium hydrogen carbonate solution, and saturated brine, dried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationThe filtrate was concentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-69100ad6c9b9474bb07d7b99a9c83556
Quelldatensatz
uspto-grants-2012_09
Patentnummer
US08263607B2

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