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

HRID 570038Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 570038
[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 5.62N 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 uptake of hydrogen had ceased and NMR indicated complete reduction. The reaction mixture was filtered through a pad of Celite 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 Celite
  4. concentrationconcentrated in vacuo
  5. customThe residue was triturated with diethylether
  6. filtrationfiltered

Quellen und Nachweise

ORD-Eintrag
ord-c8a6b478ac5f469d95d3d10bc43369bb
Quelldatensatz
uspto-grants-1988_03
Patentnummer
US04734508

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