3-Oxo-azetidine-1-carboxylic acid tert-butyl ester → 3-(3-Oxo-4-pyrimidin-2-yl-piperazin-1-yl)-azetidine-1-carboxylic acid tert-butyl ester

HRID 473593

Reaktionsgleichung

Reaktionsgleichung von HRID 473593
C(O[C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[N:19]=[CH:18][CH:17]=[CH:16][N:15]=2)[C:10](=[O:20])[CH2:9]1)=O)(C)(C)C.[C:21]([N:28]1[CH2:31]C(=O)[CH2:29]1)([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22].[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>C(O)(C(F)(F)F)=O.C(Cl)Cl.ClCCCl.CC(O)=O>[C:24]([O:23][C:21]([N:28]1[CH2:31][CH:6]([N:8]2[CH2:13][CH2:12][N:11]([C:14]3[N:15]=[CH:16][CH:17]=[CH:18][N:19]=3)[C:10](=[O:20])[CH2:9]2)[CH2:29]1)=[O:22])([CH3:27])([CH3:26])[CH3:25]

Komponenten

8

Edukt 3

HCID 15194043-Oxo-azetidine-1-carboxylic acid tert-butyl esterHCID 5049666Sodium triacetoxyborohydrideHCID 668236883-Oxo-4-pyrimidin-2-yl-piperazine-1-carboxylic acid tert-butyl ester

Produkt 1

HCID 668362493-(3-Oxo-4-pyrimidin-2-yl-piperazin-1-yl)-azetidine-1-carboxylic acid tert-butyl esterAusbeute 10,5 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 111,2-DichloroethaneLösungsmittelHCID 176Acetic AcidLösungsmittelHCID 6344DichloromethaneLösungsmittelHCID 6422Trifluoroacetic acidLösungsmittel

Versuchsvorschrift

A solution of intermediate 3b (120 mg, 0.43 mmol) in TFA (0.75 mL) and CH2Cl2 (3 mL) was stirred at room temperature for 1.5 h. The solution was concentrated. The resulting residue was stirred with N-Boc-azetidin-3-one 1a (81 mg, 0.47 mmol) and Na(OAc)3BH (100, 0.47 mmol) in 1,2-dichloroethane (4 mL) and HOAc (0.2 mL) at room temperature overnight. The reaction was quenched with aq. NaHCO3. The resulting mixture was extracted with CH2Cl2. The organic solution was dried over Na2SO4 and concentrated. Purification by column chromatography (silica gel, 3% MeOH/CH2Cl2) gave intermediate 3c as light yellow solid (15 mg).

Aufarbeitung

  1. concentrationThe solution was concentrated
  2. customThe reaction was quenched with aq. NaHCO3
  3. extractionThe resulting mixture was extracted with CH2Cl2
  4. dry with materialThe organic solution was dried over Na2SO4
  5. concentrationconcentrated
  6. customPurification by column chromatography (silica gel, 3% MeOH/CH2Cl2)

Quellen und Nachweise

ORD-Eintrag
ord-e2272eb4ff46483387dd6f0643ba0185
Quelldatensatz
uspto-grants-2014_01
Patentnummer
US08637498B2

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