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

HRID 570038노트

반응식

HRID 570038 반응식
[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

참가 물질

5

반응물 2

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

생성물 1

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

시약·촉매·용매 2

HCID 82844Platinum oxide (PtO)촉매HCID 702Ethanol용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-c8a6b478ac5f469d95d3d10bc43369bb
출처 데이터셋
uspto-grants-1988_03
특허 번호
US04734508

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