(4S)-5,5-Diphenyl-4-(propan-2-yl)-1,3-oxazolidin-2-one → (S)-2-Amino-3-methyl-1,1-diphenylbutane

HRID 1246377

Reaktionsgleichung

Reaktionsgleichung von HRID 1246377
[CH:1]([C@H:4]1[C:8]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)OC(=O)[NH:5]1)([CH3:3])[CH3:2].[H][H]>CO.CC(O)=O.[Pd]>[NH2:5][C@@H:4]([CH:1]([CH3:3])[CH3:2])[CH:8]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Komponenten

5

Edukt 2

HCID 9838646(4S)-5,5-Diphenyl-4-(propan-2-yl)-1,3-oxazolidin-2-oneHCID 178418361HCID 178418361, Verbindung

Produkt 1

HCID 9794746(S)-2-Amino-3-methyl-1,1-diphenylbutaneAusbeute 72,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 10129899Acetic acid methanolLösungsmittel

Versuchsvorschrift

A solution of (S)-4-isopropyl-5,5-diphenyl-2-oxazolidinone (3) (2.9 g, 10.31 mmol) in MeOH/AcOH and a 10% Pd (435 mg, 4.09 mmol) on activated carbon was shaken for 68 h under 4–5 atm pressure of hydrogen at room temperature. The catalyst was filtered off over Hyflo Super Cell and organic solvents were evaporated under reduced pressure. The resulting residue was treated with HCl (2.0 M, 50 ml), stirred for 2 h at room temperature, made basic with NaOH pellets, and saturated with K2CO3 and NaCl. Organic compounds were then extracted into AcOEt (3×100 ml), dried over MgSO4/K2CO3 and concentrated under reduced pressure to obtain a crude product. Re-crystallisation from petroleum ether gave the title compound (4) (1.79 g, 72%) as a light-brown solid. m.p. 71–72° C. [α]D25=−4.19° (c, 0.1097 in CHCl3). δH 0.78 (3H, d, 3J=6.60 Hz, CH3), 0.91 (3H, d, 3J=7.20 Hz, CH3), 1.26 (2H, broad s, NH2), 1.62 (1H, ds, CHMe2), 3.45 (1H, dd, 3J=10.5 and 2.40 Hz, CH—NH2), 3.70 (1H, d, 3J=10.5 Hz, CH—Ph2), 7.00–7.40 (10H, m, Ar—H). δC 14.2 and 21.5 (CH3), 28.9 (CH—Me2), 58.1 and 58.9 (CH—NH2 and CH—Ph2), 126.5, 126.7, 128.2, 128.5, 128.8 and 129.0 (o-, m- and p-Ar), 143.5 (2×α-Ar). Anal. Calcld for C17H21N: C 85.30; H 8.84; N 5.85. Found: C 85.12; H 8.91; N 5.96. ir 3361 (NH2). m/e (CI—CH4) 240 (MH+, 8%), 72 (100%).

Aufarbeitung

  1. filtrationThe catalyst was filtered off over Hyflo Super Cell and organic solvents
  2. customwere evaporated under reduced pressure
  3. additionThe resulting residue was treated with HCl (2.0 M, 50 ml)
  4. extractionOrganic compounds were then extracted into AcOEt (3×100 ml)
  5. dry with materialdried over MgSO4/K2CO3
  6. concentrationconcentrated under reduced pressure
  7. customto obtain a crude product

Quellen und Nachweise

ORD-Eintrag
ord-b438dce7dcba4ca88085423ad3aa4d3b
Quelldatensatz
uspto-grants-2006_10
Patentnummer
US07126028B1

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