Pyrrolidine → (1S,trans) 1-[(2hydroxymethyl-1-cyclohexyl)-carbonyl]-pyrrolidine

HRID 1638401Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1638401
[C:1]1(=[O:10])[C@H:9]2[C@H:4]([CH2:5][CH2:6][CH2:7][CH2:8]2)[CH2:3][O:2]1.C[O-].[Na+].[NH:14]1[CH2:18][CH2:17][CH2:16][CH2:15]1>CO>[OH:2][CH2:3][C@H:4]1[CH2:5][CH2:6][CH2:7][CH2:8][C@@H:9]1[C:1]([N:14]1[CH2:18][CH2:17][CH2:16][CH2:15]1)=[O:10]

Komponenten

5

Edukt 3

HCID 31268PyrrolidineHCID 10942334Sodium MethoxideHCID 11126340cis-hexahydroisobenzofuran-1(3H)-one

Produkt 1

HCID 14127584(1S,trans) 1-[(2hydroxymethyl-1-cyclohexyl)-carbonyl]-pyrrolidine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

4 g of (3aS,cis) hexahydro-1-(3H)-isobenzofuranone in 20 ml of methanol and 4.76 ml of pyrrolidine with 0.386 g of sodium methylate were refluxed for 20 hours and one half of the methanol was distilled off at 50° C. under reduced pressure. Water and ice were added and the pH was adjusted to 1 by adding 2N hydrochloric acid. Extraction was done with methylene chloride and the extracts were washed with water, dried, filtered, evaporated to dryness under reduced pressure and crystallized from isopropyl ether to obtain 3.89 g of (1S,trans) 1-[(2hydroxymethyl-1-cyclohexyl)-carbonyl]-pyrrolidine melting at 115° C.

Aufarbeitung

  1. distillationone half of the methanol was distilled off at 50° C. under reduced pressure
  2. additionWater and ice were added
  3. additionby adding 2N hydrochloric acid
  4. extractionExtraction
  5. washthe extracts were washed with water
  6. customdried
  7. filtrationfiltered
  8. customevaporated to dryness under reduced pressure
  9. customcrystallized from isopropyl ether

Quellen und Nachweise

ORD-Eintrag
ord-9342c11d70c541e3894086d32d0d2bb1
Quelldatensatz
uspto-grants-1989_11
Patentnummer
US04879392

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