Propanal → 4-But-3-enyl-5-ethyl-2,2-diphenyl-oxazolidine-4-carboxylic acid tert-butyl ester

HRID 579522Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 579522
[C:1]([O:5][C:6](=[O:26])[CH:7]([N:12]=[C:13]([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[CH2:8][CH2:9][CH:10]=[CH2:11])([CH3:4])([CH3:3])[CH3:2].C[Si]([N-][Si](C)(C)C)(C)C.[Na+].[Cl-].C([Al+]CC)C.[CH:43](=[O:46])[CH2:44][CH3:45]>C1COCC1>[C:1]([O:5][C:6]([C:7]1([CH2:8][CH2:9][CH:10]=[CH2:11])[CH:43]([CH2:44][CH3:45])[O:46][C:13]([C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)([C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)[NH:12]1)=[O:26])([CH3:2])([CH3:3])[CH3:4]

Komponenten

6

Edukt 4

HCID 527PropanalHCID 2724254Sodium bis(trimethylsilyl)amideHCID 160669741,1-Dimethylethyl 2-[(diphenylmethylene)amino]-5-hexenoateHCID 16686102Diethyl aluminum chloride

Produkt 1

HCID 668332184-But-3-enyl-5-ethyl-2,2-diphenyl-oxazolidine-4-carboxylic acid tert-butyl esterAusbeute 86 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

While under a nitrogen atmosphere, a stirred solution of 2-(benzhydrylidene-amino)-hex-5-enoic acid tert-butyl ester (350 mg, 1 mmol) in THF (5 mL, 0.2 M) was cooled to −78° C. and carefully treated with sodium bis(trimethylsilyl)amide (2 mL, 1 M, 2 equiv). After stirring 30 min, diethyl aluminum chloride (2.4 mL, 1 M, 2.4 equiv) was added and the reaction mixture was stirred an additional 30 min. Propionaldehyde (94 μl, 1.25 mmol, 1.25 eq) was added to the solution and the cooling bath was removed. After stirring overnight the reaction mixture was cooled to 0° C. and quenched with saturated NH4Cl. The resulting solution was diluted with ethyl acetate and washed successively with water and saturated potassium sodium tartrate, dried over MgSO4, filtered and concentrated. Purification by MPLC (1-40% ethyl acetate in heptane) gave 4-but-3-enyl-5-ethyl-2,2-diphenyl-oxazolidine-4-carboxylic acid tert-butyl ester (349 mg, 0.86 mmol, 86%).

Aufarbeitung

  1. stirringthe reaction mixture was stirred an additional 30 min
  2. customthe cooling bath was removed
  3. stirringAfter stirring overnight the reaction mixture
  4. customquenched with saturated NH4Cl
  5. additionThe resulting solution was diluted with ethyl acetate
  6. washwashed successively with water and saturated potassium sodium tartrate
  7. dry with materialdried over MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customPurification by MPLC (1-40% ethyl acetate in heptane)

Quellen und Nachweise

ORD-Eintrag
ord-c5ae4b94a0f84a3eb884600a758f3701
Quelldatensatz
uspto-grants-2015_05
Patentnummer
US09040703B2

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