Trimethylsilyldiazomethane → Methyl 3-amino-3-cyclobutylpropanoate

HRID 2171853Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2171853
[NH2:1][CH:2]([CH:7]1[CH2:10][CH2:9][CH2:8]1)[CH2:3][C:4]([OH:6])=[O:5].[N+](=[CH:13][Si](C)(C)C)=[N-]>CO.C1C=CC=CC=1.CCOC(C)=O.[Cl-].[Na+].O>[NH2:1][CH:2]([CH:7]1[CH2:10][CH2:9][CH2:8]1)[CH2:3][C:4]([O:6][CH3:13])=[O:5]

Komponenten

7

Edukt 2

HCID 167693TrimethylsilyldiazomethaneHCID 247302513-Amino-3-cyclobutylpropanoic acid2×

Produkt 1

HCID 73425272Methyl 3-amino-3-cyclobutylpropanoateAusbeute 95 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 241BenzeneLösungsmittelHCID 887MethanolLösungsmittelHCID 8857Ethyl AcetateLösungsmittelHCID 57417360Sodium chloride; waterLösungsmittel

Versuchsvorschrift

To a solution of racemic 3-amino-3-cyclobutyl-propanoic acid, 48a, (0.34 g, 2.38 mmol) in MeOH (10.2 mL) and benzene (10.2 mL) was added diazomethyltrimethyl-silane (3.56 mL of 2 M solution, 7.13 mmol) and the reaction mixture was allowed to stir at room temperature under a nitrogen atmosphere overnight. The mixture was diluted with EtOAc and brine. The layers were separated and the organic phase was dried (MgSO4), filtered and concentrated in vacuo to afford 354 mg (95%) of crude product that was used without further purification: 1H NMR (400 MHz, CDCl3) δ 3.71-3.66 (m, 3H), 3.18-2.98 (m, 1H), 2.46-2.32 (m, 2H), 2.27-1.63 (m, 10H).

Aufarbeitung

  1. customThe layers were separated
  2. dry with materialthe organic phase was dried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-6fbe25dadfa4454a879c104628e750fb
Quelldatensatz
uspto-grants-2015_06
Patentnummer
US09051319B2

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