Hydrochloric Acid → (4S)-4-Cyclohexyl-L-proline--hydrogen chloride (1/1)

HRID 232191Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 232191
[C:1]1([C@H:7]2[CH2:11][NH:10][C@H:9]([C:12]([OH:14])=[O:13])[CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[ClH:15]>C(O)C.[Pt]=O>[ClH:15].[CH:1]1([C@H:7]2[CH2:11][NH:10][C@H:9]([C:12]([OH:14])=[O:13])[CH2:8]2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Komponenten

5

Edukt 2

HCID 313Hydrochloric AcidHCID 12805582(4S)-4-Phenyl-L-proline

Produkt 1

HCID 12805591(4S)-4-Cyclohexyl-L-proline--hydrogen chloride (1/1)Ausbeute 98,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 82844Platinum oxide (PtO)KatalysatorHCID 702EthanolLösungsmittel

Versuchsvorschrift

A slurry of (trans)-4-phenyl-L-proline (50 g, 0.262 moles) and platinum oxide (10 g) in absolute ethanol (1200 ml) was treated with 5.62 N ethanolic HCl (46.5 ml, 0.261 moles) and shaken until all the solid had gone into solution. The solution was then purged with argon and hydrogenated on a Parr apparatus at 50 psi overnight. After this time, the untake of hydrogen had ceased and NMR indicated complete reduction. The reaction mixture was filtered through a pad of Cellite and concentrated in vacuo. The residue was triturated with diethylether and filtered to yield 60.0 g of (trans)-4-cyclohexyl-L-proline hydrochloride as snow white crystals, m.p. 170°-171° C.

Aufarbeitung

  1. customThe solution was then purged with argon
  2. customhydrogenated on a Parr apparatus at 50 psi overnight
  3. filtrationThe reaction mixture was filtered through a pad of Cellite
  4. concentrationconcentrated in vacuo
  5. customThe residue was triturated with diethylether
  6. filtrationfiltered

Quellen und Nachweise

ORD-Eintrag
ord-95b900de59854a5e8f102f617b5a7729
Quelldatensatz
uspto-grants-1989_07
Patentnummer
US04851514

Notizen zur Reaktion

Wird geladen…