Water → 1227911-61-6

HRID 2367314Notes

Reaction equation

HRID 2367314 reaction equation
[CH3:1][CH:2]1[N:6]([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[CH2:5][CH:4]([C:14]([O:16]CC)=[O:15])[CH2:3]1.O[Li].O.O>C1COCC1>[CH3:11][C:10]([O:9][C:7]([N:6]1[CH:2]([CH3:1])[CH2:3][CH:4]([C:14]([OH:16])=[O:15])[CH2:5]1)=[O:8])([CH3:12])[CH3:13]

Participants

5

Reactant 3

HCID 962WaterHCID 168937Lithium hydroxide, monohydrateHCID 19894765HCID 19894765, compound

Product 1

HCID 585047701227911-61-6

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1-(1,1-Dimethylethyl) 3-ethyl 5-methyl-1,3-pyrrolidinedicarboxylate (1.0 g, 3.89 mmol, an estimated 3:1 mixture of cis/trans isomers) and LiOH.H2O (228 mg, 5.44 mmol, 1.4 equiv) was stirred in THF (5 mL) and water (2 mL) as a two-phase mixture at room temperature for 18 hours. The mixture was concentrated in vacuo, and the resulting residue was taken up in 15 mL of water, acidified with cold 2N HCl, and extracted with 2×50 mL of EtOAc. The organic were dried over Na2SO4, filtered and concentrated in vacuo to afford the title compound (1.03 g) as an oil. LC-MS (ES) m/z=230 [M+H]+.

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. extractionextracted with 2×50 mL of EtOAc
  3. dry with materialThe organic were dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-a98aba7aa71147a7a1821afe8e008a08
Source dataset
uspto-grants-2014_04
Patent number
US08697685B2

Reaction notes

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