Methanol → Methyl (2R,4R)-4-hydroxypyrrolidine-2-carboxylate hydrochloride

HRID 732349

반응식

HRID 732349 반응식
S(Cl)([Cl:3])=O.[OH:5][C@H:6]1[CH2:10][NH:9][C@@H:8]([C:11]([OH:13])=[O:12])[CH2:7]1.[CH3:14]O>>[ClH:3].[CH3:14][O:12][C:11]([C@H:8]1[CH2:7][C@@H:6]([OH:5])[CH2:10][NH:9]1)=[O:13]

참가 물질

4

반응물 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 440014Cis-4-Hydroxy-D-Proline

생성물 1

HCID 12764090Methyl (2R,4R)-4-hydroxypyrrolidine-2-carboxylate hydrochloride수율 82%

실험 절차

Add thionyl chloride (5.5 mL, 75.8 mmol) to an ice-cold suspension of 4-(R)-hydroxypyrrolidine-2-(R)-carboxylic acid (4.97 g, 31.9 mmol) in methanol (60 mL). Stir 10 min, then warm to room temperature and stir 3.5 h. Concentrate, add methanol, and concentrate again. Dissolve in absolute ethanol (25 mL) and precipitate with diethyl ether (50 mL) and filter. Dry cake under vacuum to give the title compound as a white solid (4.77 g, 82%).

후처리

  1. stirringstir 3.5 h
  2. concentrationConcentrate
  3. additionadd methanol
  4. concentrationconcentrate again
  5. dissolutionDissolve in absolute ethanol (25 mL)
  6. customprecipitate with diethyl ether (50 mL)
  7. filtrationfilter
  8. customDry cake under vacuum

출처 및 근거

ORD 기록
ord-ca476a49923b4c1c88f3da697bd0a4b9
출처 데이터셋
uspto-grants-2009_09
특허 번호
US07585885B2

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