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

HRID 732349

反応式

HRID 732349 の反応式
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]

参加物

4

反応物 3

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

生成物 1

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

実験手順

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%).

後処理

  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

出典と根拠

ORDレコード
ord-ca476a49923b4c1c88f3da697bd0a4b9
出典データセット
uspto-grants-2009_09
特許番号
US07585885B2

関連ノート

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