1,2-Dichloroethane → (R)-tert-butyl 3,3-dimethyl-1-oxo-1-(pyrrolidin-1-yl)butan-2-ylcarbamate

HRID 1898493Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1898493
[C:1]([NH:8][C@@H:9]([C:14]([OH:16])=O)[C:10]([CH3:13])([CH3:12])[CH3:11])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[CH:17]1[CH:18]=CC2N(O)N=[N:23][C:21]=2[CH:22]=1.C(Cl)CCl.N1CCCC1.C(N(CC)C(C)C)(C)C>CN(C=O)C>[CH3:13][C:10]([CH3:11])([CH3:12])[C@@H:9]([NH:8][C:1](=[O:2])[O:3][C:4]([CH3:5])([CH3:6])[CH3:7])[C:14](=[O:16])[N:23]1[CH2:18][CH2:17][CH2:22][CH2:21]1

Komponenten

7

Edukt 5

HCID 111,2-DichloroethaneHCID 31268PyrrolidineHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 7005057(2R)-2-{[(tert-butoxy)carbonyl]amino}-3,3-dimethylbutanoic acid

Produkt 1

HCID 67386512(R)-tert-butyl 3,3-dimethyl-1-oxo-1-(pyrrolidin-1-yl)butan-2-ylcarbamateAusbeute 83 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A 50 mL round-bottomed flask was charged with Boc-D-tert-leucine (1.00 g, 4.32 mmol), HOBT (728 mg, 4.76 mmol), EDC (912 mg, 4.76 mmol) and pyrrolidine (0.57 mL, 6.89 mmol). Then added DMF (18 mL) followed by N,N-diisopropylethylamine (1.1 ml, 6.3 mmol). The yellow reaction mixture was stirred at room temperature overnight then quenched with H2O and extracted with Et2O (2×). The combined organic layers were washed twice with H2O and once with brine then dried over Na2SO4, filtered and concentrated. The residue was purified by chromatography over 40 g SiO2 with EtOAc/hexanes (gradient: 0-30% EtOAc) to afford 1.0 g (83%) of (R)-tert-butyl 3,3-dimethyl-1-oxo-1-(pyrrolidin-1-yl)butan-2-ylcarbamate as an off-white solid.

Aufarbeitung

  1. customthen quenched with H2O
  2. extractionextracted with Et2O (2×)
  3. washThe combined organic layers were washed twice with H2O and once with brine
  4. dry with materialthen dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by chromatography over 40 g SiO2 with EtOAc/hexanes (gradient: 0-30% EtOAc)

Quellen und Nachweise

ORD-Eintrag
ord-bf202a79393e4bb0b3f5e7da3a10c419
Quelldatensatz
uspto-grants-2013_08
Patentnummer
US08518945B2

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