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

HRID 1670621Notes

Reaction equation

HRID 1670621 reaction equation
[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

Participants

4

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

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]+.

Workup

  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

Sources & evidence

ORD record
ord-bb5a527759284231a8cd762d1b47cf36
Source dataset
uspto-grants-2011_08
Patent number
US07994164B2

Reaction notes

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