Lithium Hydroxide → (2S)-1-[(tert-butoxy)carbonyl]-4,4-difluoropyrrolidine-2-carboxylic acid

HRID 1927801Notes

Reaction equation

HRID 1927801 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][C:11]([F:14])([F:13])[CH2:10][C@H:9]1[C:15]([O:17]C)=[O:16])=[O:7])([CH3:4])([CH3:3])[CH3:2].[OH-].[Li+]>C1COCC1.C(OCC)(=O)C>[C:1]([O:5][C:6]([N:8]1[CH2:12][C:11]([F:13])([F:14])[CH2:10][C@H:9]1[C:15]([OH:17])=[O:16])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 11129200N-Boc-4,4-difluoro-L-proline methyl ester

Product 1

HCID 22977458(2S)-1-[(tert-butoxy)carbonyl]-4,4-difluoropyrrolidine-2-carboxylic acidYield 100%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

Methyl (2S)—N-(tert-butyloxycarbonyl)-4,4-difluoropyrrolidine-2-carboxylate (2.2 g, 8.3 mmol) was dissolved in THF (100 ml). Aqueous lithium hydroxide (1M, 10.6 ml, 10.6 mmol) was added. After 3 h at room temperature the reaction mixture was diluted with ethyl acetate (150 ml), washed with 1M HCl, water, and brine, dried (Na2SO4) and evaporated in vacuo. The residue was purified by flash chromatography (eluant: 95% chloroform, 4% methanol, 1% acetic acid) to give an orange oil identified as the title compound (2.1 g, 8.3 mmol 100%).

Workup

  1. washwashed with 1M HCl, water, and brine
  2. dry with materialdried (Na2SO4)
  3. customevaporated in vacuo
  4. customThe residue was purified by flash chromatography (eluant: 95% chloroform, 4% methanol, 1% acetic acid)
  5. customto give an orange oil

Sources & evidence

ORD record
ord-cd2ba68a54c34d3e91ce6f4975c65ff9
Source dataset
uspto-grants-2012_05
Patent number
US08183280B2

Reaction notes

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