Triethylamine → (+)-trans-1-(3,4-Dichlorobenzamido)-2-acetoxy-7-(pyrrolidinoformamido)tetraline

HRID 322614

Reaktionsgleichung

Reaktionsgleichung von HRID 322614
[N:1]1([C:6]([NH2:8])=[O:7])[CH2:5][CH2:4][CH2:3][CH2:2]1.O=P(Cl)(Cl)Cl.C(N(CC)CC)C.[Cl:21][C:22]1[CH:23]=[C:24]([CH:43]=[CH:44][C:45]=1[Cl:46])[C:25]([NH:27][C@@H:28]1[C:37]2[C:32](=[CH:33][CH:34]=[C:35](N)[CH:36]=2)[CH2:31][CH2:30][C@H:29]1[O:39][C:40](=[O:42])[CH3:41])=[O:26]>C(Cl)Cl>[Cl:21][C:22]1[CH:23]=[C:24]([CH:43]=[CH:44][C:45]=1[Cl:46])[C:25]([NH:27][C@@H:28]1[C:37]2[C:32](=[CH:33][CH:34]=[C:35]([NH:8][C:6]([N:1]3[CH2:5][CH2:4][CH2:3][CH2:2]3)=[O:7])[CH:36]=2)[CH2:31][CH2:30][C@H:29]1[O:39][C:40](=[O:42])[CH3:41])=[O:26]

Komponenten

6

Edukt 4

HCID 8471TriethylamineHCID 24813Phosphorus oxychlorideHCID 1383351-PyrrolidinecarboxamideHCID 12042344(+)-trans-1-(3,4-Dichlorobenzamido)-2-acetoxy-7-aminotetraline

Produkt 1

HCID 21338527(+)-trans-1-(3,4-Dichlorobenzamido)-2-acetoxy-7-(pyrrolidinoformamido)tetraline

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A solution of pyrrolidine carboxamide (1.5 mL) in CH2Cl2 (25 mL) was treated with POCl3 (0.23 mL). After 1.5 h, the solution was treated with triethylamine (1 mL) and 115 (0.5 g). After stirring over night, the solvent was evaporated, the residue was treated with ice-water, the mixture neutralized, and the mixture extracted with EtOAc. The extracts were washed with brine and the solvent was dried and evaporated to give a dark oil. The oil was purified by radial chromatography eluting with 5% EtOH-CHCl3 to give a tan solid that was recrystallized from EtOAc to give a white solid (0.18 g), m.p. 229° C., dec.

Aufarbeitung

  1. customthe solvent was evaporated
  2. additionthe residue was treated with ice-water
  3. extractionthe mixture extracted with EtOAc
  4. washThe extracts were washed with brine
  5. customthe solvent was dried
  6. customevaporated
  7. customto give a dark oil
  8. customThe oil was purified by radial chromatography
  9. washeluting with 5% EtOH-CHCl3
  10. customto give a tan solid
  11. customthat was recrystallized from EtOAc

Quellen und Nachweise

ORD-Eintrag
ord-731b390b35574151a24e1a043bfda210
Quelldatensatz
uspto-grants-2001_04
Patentnummer
US06211364B1

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