Hydrochloric Acid → (S)-tert-butyl 4-(3-(1-hydroxyethyl)benzyl)piperazine-1-carboxylate

HRID 1169603Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1169603
N#N.C(N(CC)C1C=CC=CC=1)C.B.[C:15]([C:18]1[CH:19]=[C:20]([CH:36]=[CH:37][CH:38]=1)[C:21]([N:23]1[CH2:28][CH2:27][N:26]([C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])[CH2:25][CH2:24]1)=O)(=[O:17])[CH3:16].Cl>C1(C)C=CC=CC=1.CO>[OH:17][C@H:15]([C:18]1[CH:19]=[C:20]([CH:36]=[CH:37][CH:38]=1)[CH2:21][N:23]1[CH2:24][CH2:25][N:26]([C:29]([O:31][C:32]([CH3:33])([CH3:35])[CH3:34])=[O:30])[CH2:27][CH2:28]1)[CH3:16]

Komponenten

7

Edukt 4

HCID 313Hydrochloric AcidHCID 947NitrogenHCID 83312Diethylaniline-boraneHCID 68765074Tert-butyl 4-(3-acetylbenzoyl)piperazine-1-carboxylate

Produkt 1

HCID 68766191(S)-tert-butyl 4-(3-(1-hydroxyethyl)benzyl)piperazine-1-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 1140TolueneLösungsmittel3×

Versuchsvorschrift

Under a positive pressure of N2 1-1.5M solution of (S)-Methyl oxazaborolidine (0.5 mL, 5.0 mmol) was diluted in 2 mL of toluene and treated with 3.6 mL of borane-N,N-diethylaniline. The tert-butyl 4-(3-acetylbenzoyl)piperazine-1-carboxylate from above in 3 mL of anhydrous toluene was added to the above solution over 1 hour and stirred for an additional hour. The mixture was stirred at 20° C. for another hour. To the mixture was added 6 mL MeOH, 12 mL 1N HCl and the resultant mixture stirred for 20 min. The mixture was diluted with 50 mL toluene and washed with saturated NaCl (50 mL). The organic extracts were dried over Na2SO4, filtered and concentrated at reduced pressure. The residue was heated at reflux in Et2NH for 1 hour. Purification by reverse-phase HPLC to afforded (S)-tert-butyl 4-(3-(1-hydroxyethyl)benzyl)piperazine-1-carboxylate as 1.08 g of white solid.

Aufarbeitung

  1. stirringThe mixture was stirred at 20° C. for another hour
  2. washwashed with saturated NaCl (50 mL)
  3. dry with materialThe organic extracts were dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated at reduced pressure
  6. temperatureThe residue was heated
  7. temperatureat reflux in Et2NH for 1 hour
  8. customPurification by reverse-phase HPLC

Quellen und Nachweise

ORD-Eintrag
ord-a3fd5e52718b4ec9a4f3d61d45542ebb
Quelldatensatz
uspto-grants-2010_11
Patentnummer
US07825120B2

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