Aluminum(III) Chloride → 2-(3-(Di(propan-2-yl)amino)-1-phenylpropyl)-4-(hydroxymethyl)phenol

HRID 50596

Reaktionsgleichung

Reaktionsgleichung von HRID 50596
[CH:1]([N:4]([CH:27]([CH3:29])[CH3:28])[C:5](=O)[CH2:6][CH:7]([C:14]1[CH:19]=[C:18]([C:20](OC)=[O:21])[CH:17]=[CH:16][C:15]=1[O:24]C)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)([CH3:3])[CH3:2].[H-].[H-].[H-].[H-].[Li+].[Al+3].C1COCC1.[Cl-].[Al+3].[Cl-].[Cl-]>O1CCCC1>[CH:27]([N:4]([CH:1]([CH3:3])[CH3:2])[CH2:5][CH2:6][CH:7]([C:14]1[CH:19]=[C:18]([CH2:20][OH:21])[CH:17]=[CH:16][C:15]=1[OH:24])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)([CH3:29])[CH3:28]

Komponenten

5

Edukt 3

HCID 6451240Aluminum(III) ChlorideHCID 12972418(+/-)-N,N-diisopropyl-3-(2-methoxy-5-methoxycarbonylphenyl)-3-phenylpropionamideHCID 68718528lithium aluminium hydride THF

Produkt 1

HCID 99279712-(3-(Di(propan-2-yl)amino)-1-phenylpropyl)-4-(hydroxymethyl)phenol

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A solution of (±)-N,N-diisopropyl-3-(2-methoxy-5-methoxycarbonylphenyl)-3-phenylpropionamide (0.79 g, 2.0 mmol) in 20 ml of tetrahydrofuran was cooled to 5° C. and then treated with 2.5 ml of 1M LiAlH4/THF. After stirring at room temperature for 18 hrs. finely powdered aluminium chloride (0.3 g) was added and stirring was continued for additional 4 hrs. The reaction was quenched at 5° C. by the dropwise addition of water followed by aqueous sodium hydroxide solution. The mixture was diluted with diethyl ether (150 ml) and the organic phase was washed with half saturated brine, dried (sodium sulphate), and evaporated to dryness to give the title compound as a solid off-white foam. Tlc (2) 0.16, m.p. 48-51° C. A portion of the material was converted into the hydrochloride (ethereal hydrochloric acid), m.p. 186-189° C. (dec.).

Aufarbeitung

  1. stirringstirring
  2. waitwas continued for additional 4 hrs
  3. customThe reaction was quenched at 5° C. by the dropwise addition of water
  4. additionThe mixture was diluted with diethyl ether (150 ml)
  5. washthe organic phase was washed with half saturated brine
  6. dry with materialdried (sodium sulphate)
  7. customevaporated to dryness

Quellen und Nachweise

ORD-Eintrag
ord-5f12306441c344ecbf57874da1e4b96e
Quelldatensatz
uspto-grants-2004_03
Patentnummer
US06713464B1

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