Aniline → HCID 10568153, Verbindung

HRID 342627

Reaktionsgleichung

Reaktionsgleichung von HRID 342627
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:8]([O:12][C:13]([NH:15][C@@H:16]([CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[CH:17]=O)=[O:14])([CH3:11])([CH3:10])[CH3:9].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClC(Cl)C>[C:2]1([NH:1][CH2:17][C@@H:16]([NH:15][C:13]([O:12][C:8]([CH3:9])([CH3:11])[CH3:10])=[O:14])[CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

5

Edukt 3

HCID 6115AnilineHCID 5049666Sodium triacetoxyborohydrideHCID 6998013tert-butyl N-[(2S)-1-oxo-3-phenylpropan-2-yl]carbamate

Produkt 1

HCID 10568153HCID 10568153, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 63651,1-DichloroethaneLösungsmittel

Versuchsvorschrift

Aniline (3.00 mL, 32.9 mmol) was dissolved in dichloroethane under nitrogen. The product from Step B was added (7.0 g, 29.91) and the reaction stirred for 1 h at room temperature. Sodium triacetoxyborohydride (9.51 g, 44.86 mmol) was added, and the pH adjusted to 5. The reaction was stirred overnight, then quenched with saturated sodium bicarbonate solution. The aqueous layer was removed, the organic phase washed with saturated brine and dried over magnesium sulfate. The title compound was obtained after chromatography on silica get with 8% ethyl acetate in hexane.

Aufarbeitung

  1. stirringThe reaction was stirred overnight
  2. customquenched with saturated sodium bicarbonate solution
  3. customThe aqueous layer was removed
  4. washthe organic phase washed with saturated brine
  5. dry with materialdried over magnesium sulfate

Quellen und Nachweise

ORD-Eintrag
ord-f57ec193bbda4bb2aa202df914e8578b
Quelldatensatz
uspto-grants-1999_01
Patentnummer
US05859012

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