Acetic Acid → N-(5-bromothiazol-2-yl)-cyclopropylmethylamine

HRID 1670536Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1670536
C(O)(=O)C.[Br:5][C:6]1[S:10][C:9]([NH2:11])=[N:8][CH:7]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[CH:26]1([CH:29]=O)[CH2:28][CH2:27]1>C(Cl)Cl>[Br:5][C:6]1[S:10][C:9]([NH:11][CH2:29][CH:26]2[CH2:28][CH2:27]2)=[N:8][CH:7]=1

Komponenten

6

Edukt 4

HCID 176Acetic AcidHCID 436002-Thiazolamine, 5-bromo-HCID 123114CyclopropanecarboxaldehydeHCID 5049666Sodium triacetoxyborohydride

Produkt 1

HCID 59822318N-(5-bromothiazol-2-yl)-cyclopropylmethylamineAusbeute 75 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

Add acetic acid (2 mL, 33.4 mmol) to a mixture of 5-bromo-thiazol-2-ylamine (1 g, 5.6 mmol), sodium triacetoxyborohydride (3.5 g, 16.7 mmol) and cyclopropane carboxaldehyde (820 mg, 11.7 mmol) at room temperature under a nitrogen atmosphere. Stir the resulting solution for 1.5 h at ambient temperature. Dilute the solution with DCM (50 mL) and wash with saturated aqueous NaHCO3 (80 mL). Dry the organic layer over Na2SO4, filter and concentrate in vacuo. Purify the residue by chromatography on silica gel (40 g) eluting with hexane/EtOAc (9:1 to 7:3 gradient) to obtain the title compound (970 mg, 75%). MS (ES+) m/z: 233.1 (M+).

Aufarbeitung

  1. washwash with saturated aqueous NaHCO3 (80 mL)
  2. dry with materialDry the organic layer over Na2SO4
  3. filtrationfilter
  4. concentrationconcentrate in vacuo
  5. customPurify the residue by chromatography on silica gel (40 g)
  6. washeluting with hexane/EtOAc (9:1 to 7:3 gradient)

Quellen und Nachweise

ORD-Eintrag
ord-f3187df32cfd4517987610280afe49d7
Quelldatensatz
uspto-grants-2011_08
Patentnummer
US07994163B2

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