Tetrahydrofuran → (S)-tert-Butyl 1-phenylbut-3-en-2-ylcarbamate

HRID 643061Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 643061
[CH3:1]C(C)([O-])C.[K+].C1COCC1.[CH2:12]([C@H:19]([NH:22][C:23](=[O:29])[O:24][C:25]([CH3:28])([CH3:27])[CH3:26])[CH:20]=O)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>[Br-].C1([P+](C2C=CC=CC=2)(C2C=CC=CC=2)C)C=CC=CC=1.C1(C)C=CC=CC=1>[CH2:12]([C@H:19]([NH:22][C:23](=[O:29])[O:24][C:25]([CH3:28])([CH3:27])[CH3:26])[CH:20]=[CH2:1])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Komponenten

6

Edukt 3

HCID 8028TetrahydrofuranHCID 6998013tert-butyl N-[(2S)-1-oxo-3-phenylpropan-2-yl]carbamateHCID 23665647Potassium tert-butoxide

Produkt 1

HCID 11064740(S)-tert-Butyl 1-phenylbut-3-en-2-ylcarbamateAusbeute 49 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 74505Methyltriphenyliphosphonium bromideKatalysatorHCID 1140TolueneLösungsmittel2×

Reaktionsbedingungen

Temperatur
25 °C

Versuchsvorschrift

Triphenyl methylphosphonium bromide (13.1 g, 0.037 mol) was suspended in toluene (150 mL) and was treated with 1M potassium tert-butoxide in THF (28.8 mL, 0.8 equivalents) at 25° C. for 16 hrs. This solution was added dropwise to a suspension of Example 4C in toluene (100 mL) at −78° C. over 15 min. After 1.5 h, the mixture was warmed to 25° C. and partitioned between saturated ammonium chloride (100 mL) and ethyl acetate. The organic layer was washed with brine, dried over sodium sulfate, and the solvents were evaporated. The oil was redissolved in ether:hexanes (10 mL, 1:1) and filtered to remove triphenylphosphine oxide. The filtrate was evaporated and the crude residue was purified using ethyl acetate:hexanes (1:6) to give 2.4 g (49%) of the title compound.

Aufarbeitung

  1. custompartitioned between saturated ammonium chloride (100 mL) and ethyl acetate
  2. washThe organic layer was washed with brine
  3. dry with materialdried over sodium sulfate
  4. customthe solvents were evaporated
  5. dissolutionThe oil was redissolved in ether
  6. filtrationhexanes (10 mL, 1:1) and filtered
  7. customto remove triphenylphosphine oxide
  8. customThe filtrate was evaporated
  9. customthe crude residue was purified

Quellen und Nachweise

ORD-Eintrag
ord-88a25d84a77f4dc1af258e81d3912eab
Quelldatensatz
uspto-grants-2010_04
Patentnummer
US07696226B2

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