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

HRID 81392

反応式

HRID 81392 の反応式
[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

参加物

4

反応物 3

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

生成物 1

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

反応条件

温度
0 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-c8cd2170bd6c4e7e91f7981f70c83f6d
出典データセット
uspto-grants-2014_09
特許番号
US08846694B2

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