Cyclobutanone → Tert-butyl 4-cyclobutylpiperazine-1-carboxylate

HRID 574166Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 574166
[N:1]1([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.[C:14]1(=O)[CH2:17][CH2:16][CH2:15]1.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>C(Cl)CCl>[CH:14]1([N:4]2[CH2:5][CH2:6][N:1]([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[CH2:2][CH2:3]2)[CH2:17][CH2:16][CH2:15]1

Komponenten

5

Edukt 3

HCID 14496CyclobutanoneHCID 143452tert-Butyl piperazine-1-carboxylateHCID 5049666Sodium triacetoxyborohydride

Produkt 1

HCID 57423951Tert-butyl 4-cyclobutylpiperazine-1-carboxylateAusbeute 100 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 111,2-DichloroethaneLösungsmittel

Versuchsvorschrift

To a solution of compound tert-butyl piperazine-1-carboxylate (37.2 g, 200 mmol) in ClCH2CH2Cl (500 mL) was added cyclobutanone (21 g, 300 mmol) and NaBH(OAc)3 (84.8 g, 400 mmol). The reaction mixture was stirred at rt for 16 h, quenched with saturated aq. Na2CO3 (500 mL) and extracted with DCM (3×500 mL). The combined organic layers were washed with brine (50 mL), dried, filtered and concentrated under reduced pressure to afford the desired compound tert-butyl 4-cyclobutylpiperazine-1-carboxylate (48 g, 100%) [LCMS: Rt=1.67 min, m/z 241.2 (M+H)+].

Aufarbeitung

  1. customquenched with saturated aq. Na2CO3 (500 mL)
  2. extractionextracted with DCM (3×500 mL)
  3. washThe combined organic layers were washed with brine (50 mL)
  4. customdried
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-09f2274ce4bc4703aff7a8fbd5e1d806
Quelldatensatz
uspto-grants-2015_05
Patentnummer
US09034874B2

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