Acetic Acid → (2S,5R)-1-benzyl-2,5-dimethyl-4-(3,3,3-trifluoropropyl)piperazine

HRID 1927009

Reaktionsgleichung

Reaktionsgleichung von HRID 1927009
[CH2:1]([N:8]1[CH2:13][C@@H:12]([CH3:14])[NH:11][CH2:10][C@@H:9]1[CH3:15])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[F:16][C:17]([F:22])([F:21])[CH2:18][CH:19]=O.CC(O)=O.C([BH3-])#N.[Na+]>C1COCC1.CO>[CH2:1]([N:8]1[CH2:13][C@@H:12]([CH3:14])[N:11]([CH2:19][CH2:18][C:17]([F:22])([F:21])[F:16])[CH2:10][C@@H:9]1[CH3:15])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

7

Edukt 4

HCID 176Acetic AcidHCID 680283,3,3-TrifluoropropanalHCID 5003444Sodium cyanoborohydrideHCID 23402345(2S,5R)-1-Benzyl-2,5-dimethylpiperazine

Produkt 1

HCID 57519197(2S,5R)-1-benzyl-2,5-dimethyl-4-(3,3,3-trifluoropropyl)piperazineAusbeute 92,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of (2S,5R)-1-benzyl-2,5-dimethylpiperazine (2.00 g, 7.21 mmol) in THF (10 mL), MeOH (10 mL), and TEA (1.0 mL) was added 3,3,3-trifluoropropionaldehyde (1.62 g, 14.4 mmol) and AcOH (0.826 mL, 14.4 mmol) followed by sodium cyanoborohydride (0.907 g, 14.4 mmol). The reaction was allowed to stir for 2 h, at which time the reaction was quenched with water (15 mL) then made basic with NaHCO3 and extracted with EtOAc. The organic layer was washed with brine, dried and concentrated in vacuo to yield a white powder (2.0 g, 90%). Mass Spectrum: Calcd for C16H24N2F3 (M+H): 301. Found: 301.

Aufarbeitung

  1. customwas quenched with water (15 mL)
  2. extractionextracted with EtOAc
  3. washThe organic layer was washed with brine
  4. customdried
  5. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-09b71a23782244e28b75fcc653bd1c90
Quelldatensatz
uspto-grants-2012_05
Patentnummer
US08183255B2

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