Trifluoroacetic acid → 7-Benzyl-2-oxa-7-azaspiro[4.4]nonan-1-one

HRID 1197825Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1197825
[CH2:1]([N:8]([CH2:14]OC)[CH2:9][Si](C)(C)C)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:17]=[C:18]1[CH2:23][CH2:22][O:21][C:19]1=[O:20].FC(F)(F)C(O)=O>ClCCl>[CH2:1]([N:8]1[CH2:9][CH2:17][C:18]2([C:19](=[O:20])[O:21][CH2:22][CH2:23]2)[CH2:14]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Komponenten

5

Edukt 3

HCID 6422Trifluoroacetic acidHCID 68352alpha-Methylene butyrolactoneHCID 353442Benzyl(methoxymethyl)((trimethylsilyl)methyl)amine

Produkt 1

HCID 41971377-Benzyl-2-oxa-7-azaspiro[4.4]nonan-1-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

A stirred solution of N-benzyl-N-(methoxymethyl)-N-[(trimethylsilyl)methyl]amine (D12, 160 g of 75% purity, assume 0.51 mole) and α-methylene-γ-butyrolactone (D14, 50 g, 0.51 mole) in dichloromethane (11 L) under nitrogen was cooled to 0° C. and then treated with a 1M solution of trifluoroacetic acid in dichloromethane (50ml, 0.05 mole), keeping the temperature below 5° C. The reaction mixture was allowed to warm to room temperature over 2 h, then washed with saturated sodium bicarbonate solution. The aqueous wash was extracted with dichloromethane and the organic solutions then combined, washed with brine, dried (Na2SO4) and concentrated in vacuo to leave a pale yellow oil. This was distilled in vacuo to give the title compound (D15) as a colourless oil (96 g, 81%) b.p. 160°-170° C. at 1 mmHg.

Aufarbeitung

  1. customthe temperature below 5° C
  2. washwashed with saturated sodium bicarbonate solution
  3. washThe aqueous wash
  4. extractionwas extracted with dichloromethane
  5. washwashed with brine
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated in vacuo
  8. customto leave a pale yellow oil
  9. distillationThis was distilled in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-3cd9bee9312a45d9acd0edb75624b503
Quelldatensatz
uspto-grants-1994_01
Patentnummer
US05278170

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