Methanol → (2R,4R)-methyl 4-hydroxypyrrolidine-2-carboxylate

HRID 81392

반응식

HRID 81392 반응식
[OH:1][C@H:2]1[CH2:6][NH:5][C@@H:4]([C:7]([OH:9])=[O:8])[CH2:3]1.S(Cl)(Cl)=O.[CH3:14]O>>[OH:1][C@H:2]1[CH2:6][NH:5][C@@H:4]([C:7]([O:9][CH3:14])=[O:8])[CH2:3]1

참가 물질

4

반응물 3

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

생성물 1

HCID 7020012(2R,4R)-methyl 4-hydroxypyrrolidine-2-carboxylate

반응 조건

온도
0 °C

실험 절차

7.1 30 g of (2R,4R)-4-hydroxy pyrrolidine-2-carboxylic acid are suspended in 200 ml of methanol and cooled to 0° C. Thionyl chloride (18.1 ml) is subsequently added dropwise at the same temperature distributed over an hour. The reaction mixture (RM) is warmed to room temperature (RT) over 12 h, during which a clear solution forms. The solvent is removed in vacuo, and the residue obtained is recrystallised from ether, giving 50 g of methyl (2R,4R)-4-hydroxypyrrolidine-2-carboxylate; Rt.: 0.386 min; [M+H]+146.2.

후처리

  1. waitdistributed over an hour
  2. temperatureThe reaction mixture (RM) is warmed to room temperature (RT) over 12 h
  3. customThe solvent is removed in vacuo
  4. customthe residue obtained
  5. customis recrystallised from ether

출처 및 근거

ORD 기록
ord-c8cd2170bd6c4e7e91f7981f70c83f6d
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08846694B2

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