Ethanol → Ethyl (2R,4R)-4-hydroxypyrrolidine-2-carboxylate hydrochloride

HRID 365328

반응식

HRID 365328 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.[CH2:14](O)[CH3:15]>>[ClH:3].[CH2:14]([O:12][C:11]([C@H:8]1[CH2:7][C@@H:6]([OH:5])[CH2:10][NH:9]1)=[O:13])[CH3:15]

참가 물질

4

반응물 3

HCID 702EthanolHCID 24386Thionyl ChlorideHCID 440014Cis-4-Hydroxy-D-Proline

생성물 1

HCID 12709308Ethyl (2R,4R)-4-hydroxypyrrolidine-2-carboxylate hydrochloride

실험 절차

3.27 g (27.5 mmol) of thionyl chloride was added dropwise to a suspension of cis-4-hydroxy-D-proline (3.00 g, 2.9 mmol) in ethanol (15 ml) and the mixture was refluxed for 2 hours. The mixture was concentrated, acetone was added to the residue and the solution was cooled on ice. The resultant precipitate was filtered and 4.23 g of (2R,4R)-(+)-2-(ethoxycarbonyl)-4-hydroxypyrrolidine hydrochloride was obtained as colorless needles (94.5%).

후처리

  1. temperaturethe mixture was refluxed for 2 hours
  2. concentrationThe mixture was concentrated
  3. additionacetone was added to the residue
  4. temperaturethe solution was cooled on ice
  5. filtrationThe resultant precipitate was filtered

출처 및 근거

ORD 기록
ord-c9fda451c4c64a4baef159b8914061f8
출처 데이터셋
uspto-grants-2000_10
특허 번호
US06127361

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