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

HRID 1670621노트

반응식

HRID 1670621 반응식
[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

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

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]+.

후처리

  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

출처 및 근거

ORD 기록
ord-bb5a527759284231a8cd762d1b47cf36
출처 데이터셋
uspto-grants-2011_08
특허 번호
US07994164B2

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