Isobutyraldehyde → Methyl 2-(isobutylamino)thiophene-3-carboxylate

HRID 1724658

Reaktionsgleichung

Reaktionsgleichung von HRID 1724658
[NH2:1][C:2]1[S:3][CH:4]=[CH:5][C:6]=1[C:7]([O:9][CH3:10])=[O:8].[CH:11](=O)[CH:12]([CH3:14])[CH3:13].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCl.C(O)(=O)C>[CH2:11]([NH:1][C:2]1[S:3][CH:4]=[CH:5][C:6]=1[C:7]([O:9][CH3:10])=[O:8])[CH:12]([CH3:14])[CH3:13]

Komponenten

6

Edukt 3

HCID 6561IsobutyraldehydeHCID 78381Methyl 2-amino-3-thenoateHCID 5049666Sodium triacetoxyborohydride

Produkt 1

HCID 67317044Methyl 2-(isobutylamino)thiophene-3-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 176Acetic AcidLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of methyl 2-aminothiophene-3-carboxylate (2.0 g, 12.7 mmol) in dichloromethane (40 mL) and glacial acetic acid (0.72 mL) were added isobutyraldehyde (0.87 g, 12.1 mmol) and sodium triacetoxyborohydride (4.0 g, 18.9 mmol). The reaction mixture was stirred for 18 h at room temperature and concentrated. The residue was dissolved in ethyl acetate, washed with aqueous sodium bicarbonate solution and with water, dried over anhydrous sodium sulfate and concentrated. The residual oil was purified on a silica gel flash chromatography column eluted with 5% ethyl acetate-hexane to afford the title compound as a slightly yellow oil (2.19 g, 81% yield). 1H NMR (400 MHz, CDCl3): δ 7.00 (d, 1 H), 6.18 (d, 1 H), 3.80 (s, 3 H), 3.20 (m, 2 H), 1.68 (m, 1 H), 1.00 (d, 6 H).

Aufarbeitung

  1. concentrationconcentrated
  2. dissolutionThe residue was dissolved in ethyl acetate
  3. washwashed with aqueous sodium bicarbonate solution and with water
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated
  6. customThe residual oil was purified on a silica gel flash chromatography column
  7. washeluted with 5% ethyl acetate-hexane

Quellen und Nachweise

ORD-Eintrag
ord-eb82c9ce6d23483caa90f652c375968f
Quelldatensatz
uspto-grants-2009_02
Patentnummer
US07488736B2

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