Triphenylphosphine → Tert-butyl 3-(4-(trifluoromethyl)phenoxy)pyrrolidine-1-carboxylate

HRID 72411Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 72411
[C:1]([N:8]1[CH2:12][CH2:11][CH:10]([OH:13])[CH2:9]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[F:14][C:15]([F:24])([F:23])[C:16]1[CH:21]=[CH:20][C:19](O)=[CH:18][CH:17]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O>O1CCCC1>[F:14][C:15]([F:24])([F:23])[C:16]1[CH:21]=[CH:20][C:19]([O:13][CH:10]2[CH2:11][CH2:12][N:8]([C:1]([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2])[CH2:9]2)=[CH:18][CH:17]=1

Komponenten

6

Edukt 4

HCID 11776TriphenylphosphineHCID 678744-(Trifluoromethyl)phenolHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 44169391-Boc-3-pyrrolidinol

Produkt 1

HCID 24902565Tert-butyl 3-(4-(trifluoromethyl)phenoxy)pyrrolidine-1-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a stirred solution of 1-Boc-3-pyrrolidinol (1 g, 5.34 mmol; available from Sigma-Aldrich #706620) and 4-(Trifluoromethyl)phenol (0.86 g, 5.34 mmol) in dry tetrahydrofuran (10 ml), Triphenylphosphine (1.54 g, 5.87 mmol) and diisopropyl azodicarboxylate (1.15 ml, 5.87 mmol) were added. The reaction mixture was stirred at room temperature for 2 days. Solvents were evaporated in vacuo and the residue was loaded on SPE-Si (25 g) cartridge and purified eluting with a mixture petroleum ether/ethylacetate (from 100/0 to 80/20). Collected fractions gave, after evaporation, the title compound (D34) (1.8 g).

Aufarbeitung

  1. customSolvents were evaporated in vacuo
  2. custompurified
  3. washeluting with a mixture petroleum ether/ethylacetate (from 100/0 to 80/20)
  4. customCollected fractions gave
  5. customafter evaporation

Quellen und Nachweise

ORD-Eintrag
ord-7e2430bfb7b048368c6d1ee40a746ebb
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08828987B2

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