Trimethylamine → 1-benzyl-3-(BOC-amino)-3-trifluoromethylpyrrolidine

HRID 1887

Reaktionsgleichung

Reaktionsgleichung von HRID 1887
[CH2:1]([N:8]1[CH2:12][CH2:11][C:10]([C:16]([F:19])([F:18])[F:17])(C(O)=O)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:27])C=CC=CC=1.C[N:38]([CH3:40])C.[C:41]([OH:45])([CH3:44])([CH3:43])[CH3:42]>>[CH2:1]([N:8]1[CH2:12][CH2:11][C:10]([NH:38][C:40]([O:45][C:41]([CH3:44])([CH3:43])[CH3:42])=[O:27])([C:16]([F:17])([F:18])[F:19])[CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Komponenten

5

Edukt 4

HCID 1146TrimethylamineHCID 6386tert-ButanolHCID 199401P,P-Diphenylphosphinic azideHCID 196913671-Benzyl-3-(trifluoromethyl)pyrrolidine-3-carboxylic acid

Produkt 1

HCID 196914881-benzyl-3-(BOC-amino)-3-trifluoromethylpyrrolidineAusbeute 96,7 %

Versuchsvorschrift

A mixture of 1.42 g of the compound from step 454a, 1.71 g of diphenylphosphoryl azide, 12.3 g of t-butanol and 0.627 g of trimethyl amine was heated at reflux under N2 for 24 hours. The mixture was concentrated to dryness, and the residue was dissolved in methylene chloride. The solution was washed with satd. NaHCO3 and water, then concentrated. The residue was chromatographed on silica gel to give 1.73 g of the title compound.

Aufarbeitung

  1. temperaturewas heated
  2. temperatureat reflux under N2 for 24 hours
  3. concentrationThe mixture was concentrated to dryness
  4. dissolutionthe residue was dissolved in methylene chloride
  5. washThe solution was washed with satd
  6. concentrationNaHCO3 and water, then concentrated
  7. customThe residue was chromatographed on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-3c14aa7c3cf94af8afc09046f03b475b
Quelldatensatz
uspto-grants-1998_03
Patentnummer
US05726182

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