Lithium Hydroxide → (S)-1-(3,4,5-trimethoxybenzoyl)-3-(3,4-dichlorophenyl)-3-(2-hydroxyethyl)pyrrolidine

HRID 637026Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 637026
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:27]=[C:28]([O:32][CH3:33])[C:29]=1[O:30][CH3:31])[C:6]([N:8]1[CH2:12][CH2:11][C:10]([C:19]2[CH:24]=[CH:23][C:22]([Cl:25])=[C:21]([Cl:26])[CH:20]=2)([CH2:13][CH2:14][O:15]C(=O)C)[CH2:9]1)=[O:7].[OH-].[Li+]>CO.ClCCl>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:27]=[C:28]([O:32][CH3:33])[C:29]=1[O:30][CH3:31])[C:6]([N:8]1[CH2:12][CH2:11][C@@:10]([C:19]2[CH:24]=[CH:23][C:22]([Cl:25])=[C:21]([Cl:26])[CH:20]=2)([CH2:13][CH2:14][OH:15])[CH2:9]1)=[O:7]

Komponenten

5

Edukt 2

HCID 3939Lithium HydroxideHCID 184645531-(3,4,5-Trimethoxybenzoyl)-3-(3,4-dichlorophenyl)-3-(2-acetoxyethyl)pyrrolidine

Produkt 1

HCID 53964965(S)-1-(3,4,5-trimethoxybenzoyl)-3-(3,4-dichlorophenyl)-3-(2-hydroxyethyl)pyrrolidine

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

Combine (+)-1-(3,4,5-trimethoxybenzoyl)-3-(3,4-dichlorophenyl)-3-(2-acetoxyethyl)pyrrolidine (670 mg, 1.35 mmol) and aqueous lithium hydroxide solution (4.2 mL, 1M) in methanol (15 mL). After 3.5 hours, concentrate in vacuo to give a residue. Dissolve the residue in dichloromethane and extract with 1M hydrochloric acid solution and saturated sodium bicarbonate solution. Dry the organic layer over MgSO4, filter, and concentrate in vacuo to obtain a residue. The residue was dried under high vacuum for 18 hours to give (S)-1-(3,4,5-trimethoxybenzoyl)-3-(3,4-dichlorophenyl)-3-(2-hydroxyethyl)pyrrolidine: Rf=0.11 (silica gel, ethyl acetate).

Aufarbeitung

  1. concentrationconcentrate in vacuo
  2. customto give a residue
  3. extractionextract with 1M hydrochloric acid solution and saturated sodium bicarbonate solution
  4. dry with materialDry the organic layer over MgSO4
  5. filtrationfilter
  6. concentrationconcentrate in vacuo
  7. customto obtain a residue
  8. customThe residue was dried under high vacuum for 18 hours

Quellen und Nachweise

ORD-Eintrag
ord-d421daff96d4437a887f1e28ee15b8cc
Quelldatensatz
uspto-grants-2001_02
Patentnummer
US06194406B1

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