Red-Al → HCID 59201304, Verbindung

HRID 451765

Reaktionsgleichung

Reaktionsgleichung von HRID 451765
[CH:1]1([CH2:7][C@H:8]([NH:14][C:15](=[O:21])[O:16][C:17]([CH3:20])([CH3:19])[CH3:18])[C:9]([NH:11][CH2:12][CH3:13])=O)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.COCCO[AlH2-]OCCOC.[Na+]>C1(C)C=CC=CC=1>[CH:1]1([CH2:7][C@H:8]([NH:14][C:15](=[O:21])[O:16][C:17]([CH3:20])([CH3:19])[CH3:18])[CH2:9][NH:11][CH2:12][CH3:13])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Komponenten

4

Edukt 2

HCID 16684438Red-AlHCID 59201513(S)-tert-butyl 3-cyclohexyl-1-(ethylamino)-1-oxopropan-2-ylcarbamate

Produkt 1

HCID 59201304HCID 59201304, VerbindungAusbeute 79,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

To a solution of (S)-tert-butyl 3-cyclohexyl-1-(ethylamino)-1-oxopropan-2-ylcarbamate (444 mg, 1.49 mmol) in anhydrous toluene at 0° C. was added Red-Al (65%, 1.39 g, 1.36 mL, 4.47 mmol) over 20 min. After the addition, the reaction was allowed to stir at rt overnight. The reaction was cooled to 0° C. and quenched with Na2SO4.10H2O. The resulting mixture was stirred for 2-3 h, filtered through Celite, and washed with THF (200 mL). The filtrate was dried and concentrated to give crude product (S)-tert-butyl 1-cyclohexyl-3-(ethylamino)propan-2-ylcarbamate (338 mg, 45% over 2 steps). MS ESI +ve m/z 285 (M+H).

Aufarbeitung

  1. additionAfter the addition
  2. temperatureThe reaction was cooled to 0° C.
  3. customquenched with Na2SO4.10H2O
  4. stirringThe resulting mixture was stirred for 2-3 h
  5. filtrationfiltered through Celite
  6. washwashed with THF (200 mL)
  7. customThe filtrate was dried
  8. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-c9517456e64b43898ec262b4b68de204
Quelldatensatz
uspto-grants-2013_07
Patentnummer
US08487108B2

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