4-Tert-Butylaniline → 2-[2-(4-Tert-butyl-phenylamino)-ethyl]-6-nitro-benzoic acid methyl ester

HRID 133110Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 133110
[CH3:1][O:2][C:3](=[O:16])[C:4]1[C:9]([CH2:10][CH:11]=O)=[CH:8][CH:7]=[CH:6][C:5]=1[N+:13]([O-:15])=[O:14].[C:17]([C:21]1[CH:27]=[CH:26][C:24]([NH2:25])=[CH:23][CH:22]=1)([CH3:20])([CH3:19])[CH3:18].[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>C(Cl)Cl>[CH3:1][O:2][C:3](=[O:16])[C:4]1[C:5]([N+:13]([O-:15])=[O:14])=[CH:6][CH:7]=[CH:8][C:9]=1[CH2:10][CH2:11][NH:25][C:24]1[CH:26]=[CH:27][C:21]([C:17]([CH3:20])([CH3:19])[CH3:18])=[CH:22][CH:23]=1

Komponenten

5

Edukt 3

HCID 698614-Tert-ButylanilineHCID 5049666Sodium triacetoxyborohydrideHCID 866906922-Nitro-6-(2-oxoethyl)benzoic Acid Methyl Ester

Produkt 1

HCID 691591522-[2-(4-Tert-butyl-phenylamino)-ethyl]-6-nitro-benzoic acid methyl ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of the aldehyde (Step B, 0.51 g, 2.3 mmol, 1 eq) and CH2Cl2 (30 mL) was added 4-t-butyl-aniline (0.36 mL, 2.3 mmol, 1 eq) and NaBH(OAc)3 (1.5 g, 6.8 mmol, 3.0 eq). The mixture was stirred at RT for 18 h then quenched with H2O. The mixture was extracted with EtOAc, the organic layer was washed with brine, dried (MgSO4) and concentrated in vacuo to give an orange oil. Purification by silica flash chromatography gave the desired compound as a yellow-orange foam. MS m/e 357 (M+H)+. Calc'd for C20H24N2O4-356.42.

Aufarbeitung

  1. customthen quenched with H2O
  2. extractionThe mixture was extracted with EtOAc
  3. washthe organic layer was washed with brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated in vacuo
  6. customto give an orange oil
  7. customPurification by silica flash chromatography

Quellen und Nachweise

ORD-Eintrag
ord-19c51f58e8fc491a97da71dd17bc8f8c
Quelldatensatz
uspto-grants-2008_06
Patentnummer
US07390820B2

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