Sodium Bicarbonate → (r)-5-(4-Chlorophenyl)-3,4-dihydro-2h-pyrrole-2-carboxylic acid ethyl ester

HRID 16344Notes

Reaction equation

HRID 16344 reaction equation
Cl.C(OCC)(=O)C.[CH2:8]([O:10][C:11](=[O:32])[C@H:12]([NH:24]C(OC(C)(C)C)=O)[CH2:13][CH2:14][C:15]([C:17]1[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][CH:18]=1)=O)[CH3:9].C(=O)([O-])O.[Na+]>C(OCC)(=O)C>[CH2:8]([O:10][C:11]([C@H:12]1[CH2:13][CH2:14][C:15]([C:17]2[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][CH:18]=2)=[N:24]1)=[O:32])[CH3:9]

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 21866389Hydrogen chloride-ethyl acetateHCID 67371186ethyl (R)-2-tert-butoxycarbonylamino-5-(4-chlorophenyl)-5-oxopentanoate

Product 1

HCID 67463342(r)-5-(4-Chlorophenyl)-3,4-dihydro-2h-pyrrole-2-carboxylic acid ethyl esterYield 91.8%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

A 4 N hydrochloric acid-ethyl acetate solution (30 mL) was dropwise added to an ethyl acetate solution (30 mL) of (R)-2-tert-butoxycarbonylamino-5-(4-chlorophenyl)-5-oxopentanoic acid ethyl ester (5.6 g) at room temperature. The resulting reaction solution was stirred at room temperature for 2 hr and concentrated under reduced pressure to give 5.0 g of a yellow oily substance. To an ethyl acetate solution (100 mL) of this crude product, a saturated sodium hydrogencarbonate aqueous solution (100 mL) was dropwise added. The resulting reaction solution was stirred at room temperature for 20 min and then extracted with ethyl acetate. The extract solution was washed with saturated saline, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure to give 3.5 g of the title compound as a light yellow oily substance. The physical property values of this compound were as follows:

Workup

  1. customThe resulting reaction solution
  2. concentrationconcentrated under reduced pressure
  3. customto give 5.0 g of a yellow oily substance
  4. customThe resulting reaction solution
  5. stirringwas stirred at room temperature for 20 min
  6. extractionextracted with ethyl acetate
  7. washThe extract solution was washed with saturated saline
  8. dry with materialdried over anhydrous magnesium sulfate
  9. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-252aba2b43aa49ba87e96118c41cf437
Source dataset
uspto-grants-2010_06
Patent number
US07737141B2

Reaction notes

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