Triphenylphosphine → (S)-2-(1-Benzyl-1H-tetrazol-5-yl)-pyrrolidine-1-carboxylic acid benzyl ester

HRID 1970649Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1970649
[CH2:1]([O:8][C:9]([N:11]1[CH2:15][CH2:14][CH2:13][C@H:12]1[C:16](=O)[NH:17][CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C.C[Si]([N:63]=[N+:64]=[N-:65])(C)C.N([O-])=O.[Na+]>C(#N)C.O>[CH2:1]([O:8][C:9]([N:11]1[CH2:15][CH2:14][CH2:13][C@H:12]1[C:16]1[N:17]([CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[N:65]=[N:64][N:63]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

8

Edukt 5

HCID 11776TriphenylphosphineHCID 78378AzidotrimethylsilaneHCID 690250(S)-2-Benzylcarbamoyl-pyrrolidine-1-carboxylic acid benzyl esterHCID 5363146Diisopropyl azodicarboxylateHCID 23668193Sodium Nitrite

Produkt 1

HCID 66857129(S)-2-(1-Benzyl-1H-tetrazol-5-yl)-pyrrolidine-1-carboxylic acid benzyl ester

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

To a suspension of 1.50 g (S)-2-Benzylcarbamoyl-pyrrolidine-1-carboxylic acid benzyl ester and 2.91 g triphenylphosphine in 30 ml acetonitrile were added dropwise at 0° C. 2.3 ml diisopropylazodicarboxylate and after 2 minutes 1.5 ml trimethylsilylazide over a period of 20 minutes. After 30 minutes the mixture was allowed to warm to RT and stirred for 12 h. The mixture was cooled to 0° C. and 1.5 ml aqueous sodium nitrite (2.9 M) were added, after 30 minutes a solution of 2.4 g ceric ammonium nitrate in 15 ml water was added and stirred for another 20 minutes. After this time the mixture was poured into ice and extracted twice with dichloromethane. The crude product thus obtained after evaporation of the solvent was purified by flash chromatography on silica eluting with ethyl acetate/heptane gradient. Yield: 494 mg colorless foam.

Aufarbeitung

  1. additionwere added dropwise at 0° C
  2. temperatureThe mixture was cooled to 0° C.
  3. additionwas added
  4. stirringstirred for another 20 minutes
  5. additionAfter this time the mixture was poured into ice
  6. extractionextracted twice with dichloromethane

Quellen und Nachweise

ORD-Eintrag
ord-c6a6576319804ebbaa597ffb19115ede
Quelldatensatz
uspto-grants-2013_04
Patentnummer
US08426420B2

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