(2S,3S,alphaS)-t-Butyl 3-(N-allyl-alpha-methylbenzylamino)-2-hydroxy-3-phenylpropionate → (2S,4S,5S,alphaS)-2-Ethyl-3-(alpha-methylbenzyl)-4-phenyl-1,3-oxazolidine-5-carboxylic acid t-butyl ester

HRID 1637047Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1637047
[CH2:1]([N:4]([C@@H:21]([CH3:28])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[C@@H:5]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[C@H:6]([OH:14])[C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[CH:2]=[CH2:3]>C1(C)C=CC=CC=1.[Rh]Cl.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[C:10]([O:9][C:7]([C@H:6]1[O:14][C@@H:1]([CH2:2][CH3:3])[N:4]([C@@H:21]([CH3:28])[C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=2)[C@H:5]1[C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1)=[O:8])([CH3:13])([CH3:12])[CH3:11]

Komponenten

4

Edukt 1

HCID 86755227(2S,3S,alphaS)-t-Butyl 3-(N-allyl-alpha-methylbenzylamino)-2-hydroxy-3-phenylpropionate

Produkt 1

HCID 86755235(2S,4S,5S,alphaS)-2-Ethyl-3-(alpha-methylbenzyl)-4-phenyl-1,3-oxazolidine-5-carboxylic acid t-butyl esterAusbeute 83 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178479813HCID 178479813, VerbindungKatalysatorHCID 1140TolueneLösungsmittel2×

Versuchsvorschrift

To a solution of compound (27) from Example 12 (1.039 g, 2.73 mmol) in anhydrous toluene (25 ml) was added tris(triphenylphosphine) rhodium(I) chloride (126 mg, 5 mol %). This solution was refluxed for 4 hours whereafter the toluene was removed under reduced pressure. The residue was treated with diethyl ether, precipitating the catalyst, and the solution was passed through alumina grade 5. After removal of the solvent under reduced pressure, the resulting oil was purified by flash chromatography on silica gel [ethyl acetate/petroleum ether (1:19)] affording the title compound (Rf 0.40) as a colourless oil (0.86 g, 83%). δH (300 MHz; CDCl3) 7.33-7.18 (10H, m, Ph), 4.48 (1H, t, NCHO), 4.38 (1H, d, J=8.0, PhCHCH), 4.21 (1H, d, J=8.0, PhCHCH), 4.01 (1H, q, J=6.9, PhCHCH3), 1.91 (2H, m, CHCH2CH3), 1.27 (3H, d, J=6.9, PhCHCH3), 1.15 (3H, t, J=7.5, CHCH2CH3), 0.99 (9H, s, (CH3)3C).

Aufarbeitung

  1. customwas removed under reduced pressure
  2. additionThe residue was treated with diethyl ether
  3. customprecipitating the catalyst
  4. customAfter removal of the solvent under reduced pressure
  5. customthe resulting oil was purified by flash chromatography on silica gel [ethyl acetate/petroleum ether (1:19)]

Quellen und Nachweise

ORD-Eintrag
ord-ad151db2dfb64c179edb4f15a00b19e2
Quelldatensatz
uspto-grants-2000_03
Patentnummer
US06037498

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