Sodium Hydroxide → (S)-3-(4-nitrobenzoyloxy)pyrrolidine

HRID 1859443Notes

Reaction equation

HRID 1859443 reaction equation
Cl.O1CCOCC1.C(OC([N:15]1[CH2:19][CH2:18][C@H:17]([O:20][C:21](=[O:31])[C:22]2[CH:27]=[CH:26][C:25]([N+:28]([O-:30])=[O:29])=[CH:24][CH:23]=2)[CH2:16]1)=O)(C)(C)C.[OH-].[Na+]>O1CCOCC1>[N+:28]([C:25]1[CH:26]=[CH:27][C:22]([C:21]([O:20][C@H:17]2[CH2:18][CH2:19][NH:15][CH2:16]2)=[O:31])=[CH:23][CH:24]=1)([O-:30])=[O:29]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 10449656(S)-1-t-butoxycarbonyl-3-(4-nitrobenzoyloxy)pyrrolidineHCID 204431481,4-Dioxane hydrochloride

Product 1

HCID 12148704(S)-3-(4-nitrobenzoyloxy)pyrrolidine

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

4 M hydrochloric acid/dioxane (3.0 ml) was added to a solution of (S)-1-t-butoxycarbonyl-3-(4-nitrobenzoyloxy)pyrrolidine [J. Org. Chem. 59, 2289 (1994)] (1.68 g, 5 mmol) in dioxane (10 ml), and they were stirred for 2 hours. The reaction liquid was poured into 1 M-aqueous NaOH solution cooled on ice/water. After the extraction with ethyl acetate, the organic layer was dried and the solvent was evaporated under reduced pressure to obtain (S)-3-(4-nitrobenzoyloxy)pyrrolidine in the form of a light yellow oil (799 mg, 68%).

Workup

  1. customThe reaction liquid
  2. temperaturecooled on ice/water
  3. extractionAfter the extraction with ethyl acetate
  4. customthe organic layer was dried
  5. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-bcaac6f7db034e56bd0a49fdc3ac96fa
Source dataset
uspto-grants-2003_03
Patent number
US06528504B2

Reaction notes

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