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

HRID 232191Notes

Reaction equation

HRID 232191 reaction equation
[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

Participants

5

Reactant 2

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

Product 1

HCID 12805591(4S)-4-Cyclohexyl-L-proline--hydrogen chloride (1/1)Yield 98.4%

Reagents, catalysts & solvents 2

HCID 82844Platinum oxide (PtO)CatalystHCID 702EthanolSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-95b900de59854a5e8f102f617b5a7729
Source dataset
uspto-grants-1989_07
Patent number
US04851514

Reaction notes

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