Red-Al → (S)-tert-butyl 1-cyclohexyl-3-(ethylamino)propan-2-ylcarbamate

HRID 451775

Reaktionsgleichung

Reaktionsgleichung von HRID 451775
[NH2:1][C:2](=O)[C@:3]([NH:12][C:13](=[O:19])[O:14][C:15]([CH3:18])([CH3:17])[CH3:16])(C)[CH2:4][CH:5]1[CH2:10][CH2:9][CH2:8][CH2:7][CH2:6]1.CO[CH2:23][CH2:24]O[AlH2-]OCCOC.[Na+]>C1(C)C=CC=CC=1>[CH:5]1([CH2:4][C@H:3]([NH:12][C:13](=[O:19])[O:14][C:15]([CH3:16])([CH3:17])[CH3:18])[CH2:2][NH:1][CH2:23][CH3:24])[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10]1

Komponenten

4

Edukt 2

HCID 16684438Red-AlHCID 59201392(S)-tert-butyl 1-amino-3-cyclohexyl-2-methyl-1-oxopropan-2-ylcarbamate2×

Produkt 1

HCID 59201304(S)-tert-butyl 1-cyclohexyl-3-(ethylamino)propan-2-ylcarbamate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

(S)-tert-butyl 1-amino-3-cyclohexyl-2-methyl-1-oxopropan-2-ylcarbamate To a solution of (S)-tert-butyl 1-amino-3-cyclohexyl-2-methyl-1-oxopropan-2-ylcarbamate (811 mg, 2.85 mmol) in anhydrous toluene (15 mL) at 0° C. was added Red-Al (65%, 2.66 g, 2.6 mL, 8.55 mmol) within 20 min. After the addition, the reaction was allowed to be stirred at room temperature 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 (860 mg). MS ESI +ve m/z 271 (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-7963882c5a114b6dabbe11c6fa57e402
Quelldatensatz
uspto-grants-2013_07
Patentnummer
US08487108B2

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