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

HRID 570038ノート

反応式

HRID 570038 の反応式
[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

参加物

5

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 82844Platinum oxide (PtO)触媒HCID 702Ethanol溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-c8a6b478ac5f469d95d3d10bc43369bb
出典データセット
uspto-grants-1988_03
特許番号
US04734508

反応ノート

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