(alphaS)-alpha-[Bis(phenylmethyl)amino]benzenepropanal → HCID 69015925, Verbindung

HRID 1436498

Reaktionsgleichung

Reaktionsgleichung von HRID 1436498
C([Li])(CC)C.[C:6]([O:10][C:11]([N:13]1[CH2:18][CH2:17][CH2:16][CH2:15][CH:14]1[CH2:19][CH3:20])=[O:12])([CH3:9])([CH3:8])[CH3:7].[CH2:21]([N:28]([CH2:39][C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1)[C@@H:29]([CH2:32][C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)[CH:30]=[O:31])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>C(OCC)C>[C:6]([O:10][C:11]([N:13]1[CH:14]([CH2:19][CH3:20])[CH2:15][CH2:16][CH2:17][CH:18]1[CH:30]([OH:31])[C@@H:29]([N:28]([CH2:21][C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1)[CH2:39][C:40]1[CH:41]=[CH:42][CH:43]=[CH:44][CH:45]=1)[CH2:32][C:33]1[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=1)=[O:12])([CH3:9])([CH3:8])[CH3:7]

Komponenten

5

Edukt 3

HCID 9883943(alphaS)-alpha-[Bis(phenylmethyl)amino]benzenepropanalHCID 12170201tert-Butyl 2-Ethylpiperidine-1-carboxylateHCID 178418400CID 53628100

Produkt 1

HCID 69015925HCID 69015925, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3283Diethyl EtherLösungsmittel2×

Reaktionsbedingungen

Temperatur
-35 °C

Versuchsvorschrift

Add N,N,N′,N′-tetrametlhylethylenediamine (1.4 mL, 9.11 mmol), then sec-butyllithium (1.4 M in cyclohexane, 7.2 mL, 10.1 mmol) to 2-ethylpiperidine-1-carboxylic acid tert-butyl ester in diethyl ether (18 mL) at −78° C. under a nitrogen atmosphere. Warm to −35° C. and stir for 1 h. Cool to −78° C. and add (2S)-2-(dibenzylamino)-3-phenylpropanal (3.0 g, 9.11 mmol) in diethyl ether (4 mL) and stir for 30 min. Quench at −78° C. with water, warm to room temperature and extract with diethyl ether. Combine the organic layers, dry (magnesium sulfate) and concentrate. Separate the two major diastereomers of 2-((2S)-2-dibenzylaniino-1-hydroxy-3-phenylpropyl)-6-ethylpiperidine-1-carboxylic acid tert-butyl ester using normal-phase preparative HPLC (Kromasil Si 60, 10 μm, 80×180 mm; 98:2 Hexane:Acetone; 130 mL/min).

Aufarbeitung

  1. additionAdd N,N,N′,N′-tetrametlhylethylenediamine (1.4 mL, 9.11 mmol)
  2. customat −78° C.
  3. temperatureCool to −78° C.
  4. stirringstir for 30 min
  5. customQuench at −78° C. with water
  6. temperaturewarm to room temperature
  7. extractionextract with diethyl ether
  8. dry with materialdry (magnesium sulfate)
  9. concentrationconcentrate
  10. customSeparate the two major diastereomers of 2-((2S)-2-dibenzylaniino-1-hydroxy-3-phenylpropyl)-6-ethylpiperidine-1-carboxylic acid tert-butyl ester using normal-phase preparative HPLC (Kromasil Si 60, 10 μm, 80×180 mm; 98:2 Hexane:Acetone; 130 mL/min)

Quellen und Nachweise

ORD-Eintrag
ord-492cf1b5e67a4e8c8cea20c092d44c40
Quelldatensatz
uspto-grants-2009_11
Patentnummer
US07618978B2

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