Trimethylsilyl triflate → Benzyl 2,3-dihydro-1H-pyrrole-1-carboxylate

HRID 132820Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 132820
[CH2:1]([O:8][C:9]([N:11]1[CH2:15][CH2:14][CH2:13][CH:12]1OC)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C[Si](OS(C(F)(F)F)(=O)=O)(C)C>ClCCl>[CH2:1]([O:8][C:9]([N:11]1[CH:12]=[CH:13][CH2:14][CH2:15]1)=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Komponenten

4

Edukt 2

HCID 65367Trimethylsilyl triflateHCID 109224852-Methoxy-pyrrolidine-1-carboxylic acid benzyl ester

Produkt 1

HCID 11074472Benzyl 2,3-dihydro-1H-pyrrole-1-carboxylateAusbeute 75,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a cold (0° C.) solution of 2-methoxy-pyrrolidine-1-carboxylic acid benzyl ester (example 4, step 4, 500 mg, 1.0 eq.) in dichloromethane was added N-diisopropylethyl-amine (0.5 mL, 1.36 eq.) and trimethylsilyltrifluoromethanesulfonate (0.51 mL, 1.3 eq.). The reaction mixture was stirred at 0° C. for 30 min and partitioned between dichloromethane and an aqueous solution of sodium hydrogencarbonate. The aqueous layer was extracted with dichloromethane. The combined organic layers were washed with water and evaporated in vacuo and purified on silica eluting with 19:1 cyclohexane/ethyl acetate to yield 325 mg (75%) of the desired product as a colourless oil. MS (m/e): 204.5 (MH+, 100%).

Aufarbeitung

  1. custompartitioned between dichloromethane
  2. extractionThe aqueous layer was extracted with dichloromethane
  3. washThe combined organic layers were washed with water
  4. customevaporated in vacuo
  5. custompurified on silica eluting with 19:1 cyclohexane/ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-5d8791d20b284e54b14e8f9856777282
Quelldatensatz
uspto-grants-2008_06
Patentnummer
US07388095B2

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