Triphenylphosphine → HCID 18654599, Verbindung

HRID 375121

Reaktionsgleichung

Reaktionsgleichung von HRID 375121
[CH3:1][O:2][C:3](=[O:20])[C@@H:4]1[CH2:8][C@@H:7]([OH:9])[CH2:6][N:5]1[C:10]([O:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[O:11].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:40]([C:42]1[CH:47]=[CH:46][C:45](O)=[CH:44][CH:43]=1)#[N:41].CCOC(/N=N/C(OCC)=O)=O>C1COCC1>[CH3:1][O:2][C:3](=[O:20])[C@@H:4]1[CH2:8][C@H:7]([O:9][C:45]2[CH:46]=[CH:47][C:42]([C:40]#[N:41])=[CH:43][CH:44]=2)[CH2:6][N:5]1[C:10]([O:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[O:11]

Komponenten

6

Edukt 4

HCID 11776TriphenylphosphineHCID 130194-CyanophenolHCID 6884112-Methyl 1-(phenylmethyl) (2S,4R)-4-hydroxy-1,2-pyrrolidinedicarboxylateHCID 5462977Diethyl azodicarboxylate

Produkt 1

HCID 18654599HCID 18654599, VerbindungAusbeute 89 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a solution of N-carbobenzyloxy-trans-4-hydroxy-L-proline methyl ester (10.0 g, 35.8 mmol) in 200 mL of anhydrous THF under N2 was added triphenylphosphine (10.6 g, 3 9.4 mmol) and 4-cyanophenol (4.7 g, 39.4 mmol) . This solution was cooled to 0° C. and then treated with diethylazodicarboxylate (6.3 mL, 39.4 mmol), added dropwise over 30 minutes The reaction was warmed to room temperature and stirred for 2 days. The solvent was removed in vacuo and the residue chromatographed (SiO2, 30% ethyl acetate/hexanes) to provide 12.1 g (89%) of N-carbobenzyloxy-4-(cis)-(4-cyanophenoxy)-L-proline methyl ester as a colorless oil. MS.

Aufarbeitung

  1. additionadded dropwise over 30 minutes The reaction
  2. temperaturewas warmed to room temperature
  3. customThe solvent was removed in vacuo
  4. customthe residue chromatographed (SiO2, 30% ethyl acetate/hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-d581f4a9e0c24a319835f6b6689a0513
Quelldatensatz
uspto-grants-1996_01
Patentnummer
US05484780

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