p-Toluenesulfonic acid → HCID 57312488, Verbindung

HRID 5911

Reaktionsgleichung

Reaktionsgleichung von HRID 5911
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH:7]2[CH2:12][CH2:11][CH2:10][CH2:9][C:8]2=O)[CH:2]=1.[NH2:14][N:15]1[CH2:19][CH2:18][CH2:17][C@H:16]1[CH2:20][O:21][CH3:22].C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1.C(OCC)C>[CH3:22][O:21][CH2:20][C@@H:16]1[CH2:17][CH2:18][CH2:19][N:15]1[N:14]=[C:8]1[CH2:9][CH2:10][CH2:11][CH2:12][CH:7]1[C:3]1[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=1

Komponenten

6

Edukt 3

HCID 6101p-Toluenesulfonic acidHCID 7156993(S)-(-)-1-Amino-2-(methoxymethyl)pyrrolidineHCID 10976010HCID 10976010, Verbindung

Produkt 1

HCID 57312488HCID 57312488, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 1140TolueneLösungsmittelHCID 3283Diethyl EtherLösungsmittel

Versuchsvorschrift

A mixture of 2-(pyrid-3-yl)cyclohexanone (20.6 g, 117.6 mmol), [S]-(-)-1-amino-2-(methoxymethyl)pyrrolidine (`SAMP`) (15.4 g, 118 mmol) and p-toluenesulphonic acid (316 mg) was refluxed in toluene (475 ml) for 4 hours. The toluene was removed in vacuo to afford an oil which was dissolved in diethyl ether (340ml) and washed with aqueous saturated sodium bicarbonate solution (2×170 ml). The organic phase was dried over magnesium sulphate then filtered and concentrated in vacuo to afford [2S]-2-(methoxymethyl)-1-[2-(pyrid-3-yl)cyclohexylidenamino]pyrrolidine (30.8 g, 113 mmol) as a 50:50 mixture of diastereoisomers;

Aufarbeitung

  1. customThe toluene was removed in vacuo
  2. customto afford an oil which
  3. washwashed with aqueous saturated sodium bicarbonate solution (2×170 ml)
  4. dry with materialThe organic phase was dried over magnesium sulphate
  5. filtrationthen filtered
  6. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-451cf868ebf34c44bf70d7d52db70570
Quelldatensatz
uspto-grants-1993_09
Patentnummer
US05246950

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