Water → (5S)-1-(tert-Butoxycarbonyl)-5-methyl-L-proline

HRID 2038858Notes

Reaction equation

HRID 2038858 reaction equation
[CH3:1][C@@H:2]1[N:6]([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[C@H:5]([C:14]([O:16]CC)=[O:15])[CH2:4][CH2:3]1.O.[OH-].[Li+].O>C(O)C>[C:10]([O:9][C:7]([N:6]1[C@@H:2]([CH3:1])[CH2:3][CH2:4][C@H:5]1[C:14]([OH:16])=[O:15])=[O:8])([CH3:11])([CH3:12])[CH3:13]

Participants

5

Reactant 3

HCID 962WaterHCID 168937Lithium hydroxide, monohydrateHCID 69622155(2S,5S)-1-tert-butyl 2-ethyl 5-methylpyrrolidine-1,2-dicarboxylate

Product 1

HCID 15516206(5S)-1-(tert-Butoxycarbonyl)-5-methyl-L-proline

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of (2S,5S)-1-tert-butyl 2-ethyl 5-methylpyrrolidine-1,2-dicarboxylate (6.46 g, 25.1 mmol) in ethanol (20 mL) was added lithium hydroxide mono hydrate (2.11 g, 50.2 mmol) and deionized water (12 mL). The mixture was allowed to stir for 16 hours then partitioned between ethylacetate and a 1:1 mixture of saturated brine and 1N HCl. The aqueous layer was extracted an additional time with ethyl acetate. The organic layers were combined, dried with sodium sulfate and the solvent was removed in vacuo to yield (2S,5S)-1-(tert-butoxycarbonyl)-5-methylpyrrolidine-2-carboxylic acid as a white solid (quant.) and was used directly in the following step.

Workup

  1. customthen partitioned between ethylacetate
  2. additiona 1:1 mixture of saturated brine and 1N HCl
  3. extractionThe aqueous layer was extracted an additional time with ethyl acetate
  4. dry with materialdried with sodium sulfate
  5. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-1ad23cba057a41aea8f1076fe4874381
Source dataset
uspto-grants-2013_11
Patent number
US08575135B2

Reaction notes

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