Lithium Hydroxide → (3S,4R)-tert-butyl 3-(4-bromo-2-nitrophenylamino)-4-hydroxypyrrolidine-1-carboxylate

HRID 1670621ノート

反応式

HRID 1670621 の反応式
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C@@H:9]2[C@H:13]([O:14]C(=O)CCl)[CH2:12][N:11]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:10]2)=[C:4]([N+:26]([O-:28])=[O:27])[CH:3]=1.[OH-].[Li+]>CO>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C@@H:9]2[C@H:13]([OH:14])[CH2:12][N:11]([C:19]([O:21][C:22]([CH3:24])([CH3:25])[CH3:23])=[O:20])[CH2:10]2)=[C:4]([N+:26]([O-:28])=[O:27])[CH:3]=1

参加物

4

反応物 2

HCID 3939Lithium HydroxideHCID 86631935(3S,4R)-tert-butyl 3-(4-bromo-2-nitrophenylamino)-4-(2-chloroacetoxy)pyrrolidine-1-carboxylate

生成物 1

HCID 67335018(3S,4R)-tert-butyl 3-(4-bromo-2-nitrophenylamino)-4-hydroxypyrrolidine-1-carboxylate収率 101.7%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

To a solution of the (3S,4R)-tert-butyl 3-(4-bromo-2-nitrophenylamino)-4-(2-chloroacetoxy)pyrrolidine-1-carboxylate (2.20 mmol, 1.0 g) in methanol add 2.0 M aqueous lithium hydroxide (5 mL) and stir at room temperature for 3.5 h. Remove the solvent, dilute the residue with ethyl acetate (50 mL), and wash with water and brine. Dry over anhydrous sodium sulfate, filter, and evaporate the solvent. Purify by column chromatography eluting with 50% ethyl acetate in methylene chloride to obtain the title compound as a yellow solid (900 mg, 98%). APCI MS m/z 462 [M+H]+.

後処理

  1. customRemove the solvent
  2. additiondilute the residue with ethyl acetate (50 mL)
  3. washwash with water and brine
  4. dry with materialDry over anhydrous sodium sulfate
  5. filtrationfilter
  6. customevaporate the solvent
  7. customPurify by column chromatography
  8. washeluting with 50% ethyl acetate in methylene chloride

出典と根拠

ORDレコード
ord-bb5a527759284231a8cd762d1b47cf36
出典データセット
uspto-grants-2011_08
特許番号
US07994164B2

反応ノート

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