Acetic Anhydride → HCID 68915138, Verbindung

HRID 732657

Reaktionsgleichung

Reaktionsgleichung von HRID 732657
[Si]([O:8][CH2:9][CH:10]1[CH:14]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH2:13][NH:12][CH2:11]1)(C(C)(C)C)(C)C.[C:21](OC)(=[O:30])/[CH:22]=C/C1C=CC=CC=1.C(OC(=O)C)(=O)C>N1C=CC=CC=1>[C:21]([N:12]1[CH2:13][CH:14]([C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH:10]([CH2:9][OH:8])[CH2:11]1)(=[O:30])[CH3:22]

Komponenten

5

Edukt 3

HCID 7918Acetic AnhydrideHCID 637520Methyl CinnamateHCID 219128003-({[Tert-butyl(dimethyl)silyl]oxy}methyl)-4-phenylpyrrolidine

Produkt 1

HCID 68915138HCID 68915138, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1049PyridineLösungsmittel

Versuchsvorschrift

A pyridine solution of 3-({[tert-butyl(dimethyl)silyl]oxy}methyl)-4-phenylpyrrolidine which had been synthesized from methyl trans-cinnamate, in accordance with the technique of Ling et al. (“Tetrahedron”, 2001, vol. 57,p. 6579-6588) and the method of International Patent Publication WO 2000/59502, was mixed with acetic anhydride and stirred at room temperature for 2Hours. After completion of the reaction, this was concentrated under a reduced pressure with toluene azeotropy, and THF and 1 M THF solution of TBAF were added to the thus obtained residue and stirred overnight at room temperature. Thereafter, its work-up and purification were carried out in the standard method to obtain (1-acetyl-4-phenylpyrrolidin-3-yl)methanol. EP: 220.

Aufarbeitung

  1. customAfter completion of the reaction
  2. concentrationthis was concentrated under a reduced pressure with toluene azeotropy, and THF and 1 M THF solution of TBAF
  3. additionwere added to the thus obtained residue
  4. stirringstirred overnight at room temperature
  5. customThereafter, its work-up and purification

Quellen und Nachweise

ORD-Eintrag
ord-5ed27cc94cc34c569d450626b02f55b1
Quelldatensatz
uspto-grants-2009_09
Patentnummer
US07585886B2

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