Ammonium Hydroxide → Ethyl 2-amino-2-methyl-4-oxo-4-p-tolylbutanoate

HRID 1629785Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1629785
[CH3:1]/[C:2](=[CH:8]\[C:9](=[O:17])[C:10]1[CH:15]=[CH:14][C:13]([CH3:16])=[CH:12][CH:11]=1)/[C:3]([O:5][CH2:6][CH3:7])=[O:4].[NH4+:18].[OH-]>CS(C)=O.CCOC(C)=O>[NH2:18][C:2]([CH3:1])([CH2:8][C:9](=[O:17])[C:10]1[CH:15]=[CH:14][C:13]([CH3:16])=[CH:12][CH:11]=1)[C:3]([O:5][CH2:6][CH3:7])=[O:4]

Komponenten

5

Edukt 2

HCID 14923Ammonium HydroxideHCID 86685877(E)-Ethyl 2-methyl-4-oxo-4-p-tolylbut-2-enoate

Produkt 1

HCID 86685876Ethyl 2-amino-2-methyl-4-oxo-4-p-tolylbutanoateAusbeute 55,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 679Dimethyl SulfoxideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a solution of Intermediate 102A (1.067 g, 4.59 mmol) in DMSO (20 mL) under argon was added NH4OH (18.04 mL, 271 mmol) and the reaction mixture was stirred at rt overnight. The reaction mixture was diluted with EtOAc (75 mL) and washed sequentially with water (40 mL) and brine (20 mL). The organic phase was dried over MgSO4 and concentrated in vacuo to give a yellow oil. The oil was purified by silica gel chromatography (120 g silica gel) to provide the desired product (0.632 g, 55%) as a clear oil. LCMS Anal. Calc'd for C14H19NO3 249.14, found [M+H] 250.1. 1H NMR (500 MHz, CDCl3) δ 7.83 (d, J=8.25 Hz, 2H), 7.24 (d, J=7.98 Hz, 2H), 4.14 (dd, J=7.15, 2.75 Hz, 2H), 3.65 (d, J=17.61 Hz, 1H), 3.20 (d, J=17.61 Hz, 1H), 2.40 (s, 3H), 2.18-2.27 (m, 2H), 1.39 (s, 3H), 1.19 (t, J=7.01 Hz, 3H).

Aufarbeitung

  1. washwashed sequentially with water (40 mL) and brine (20 mL)
  2. dry with materialThe organic phase was dried over MgSO4
  3. concentrationconcentrated in vacuo
  4. customto give a yellow oil
  5. customThe oil was purified by silica gel chromatography (120 g silica gel)

Quellen und Nachweise

ORD-Eintrag
ord-83a9b17334c149558e2297885d4429fc
Quelldatensatz
uspto-grants-2014_07
Patentnummer
US08791091B2

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