Lithium Hydroxide → HCID 57907462, compound

HRID 1947719Notes

Reaction equation

HRID 1947719 reaction equation
[O:1]=[C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[N:3]1[C@H:4]([C:11]([O:13]C)=[O:12])[CH2:5][CH2:6]2.[Li+].[OH-]>C1COCC1>[O:1]=[C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[N:3]1[C@H:4]([C:11]([OH:13])=[O:12])[CH2:5][CH2:6]2

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 57907618HCID 57907618, compound

Product 1

HCID 57907462HCID 57907462, compoundYield 94.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 0.200 mg (1.00 mmol) of methyl (3S)-5-oxo-1,2,3,5-tetrahydroindolizine-3-carboxylate from step B above in 3 mL of THF was added 1.5 mL (1.5 mmol) of a 1.0 M aqueous LiOH solution. The resulting mixture was stirred for 2 h at ambient temperature then quenched with 2.0 mL (2.0 mmol) of a 1.0 M aqueous solution of hydrogen chloride. All volatiles were evaporated in vacuo and the aqueous phase was extracted with a 30% IPA in chloroform mixture (3×5 mL). The combined extract were washed with brine, dried over magnesium sulfate, filtered, and evaporated in vacuo to afford the title compound as a white solid (0.17 g, 92%). 1H NMR (500 MHz, CD3OD): δ 7.53 (dd, J=8.9, 7.1 Hz, 1H), 6.38-6.35 (m, 2H), 5.11 (dd, J=9.7, 2.7 Hz, 1H), 3.23-3.12 (m, 2H), 2.62-2.53 (m, 1H), 2.35-2.30 (m, 1H). LC-MS: m/z (ES) 180 (MH)+.

Workup

  1. customthen quenched with 2.0 mL (2.0 mmol) of a 1.0 M aqueous solution of hydrogen chloride
  2. customAll volatiles were evaporated in vacuo
  3. extractionthe aqueous phase was extracted with a 30% IPA in chloroform mixture (3×5 mL)
  4. extractionThe combined extract
  5. washwere washed with brine
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. customevaporated in vacuo

Sources & evidence

ORD record
ord-e07a49c195564161915e76a4791c0afe
Source dataset
uspto-grants-2013_03
Patent number
US08399480B2

Reaction notes

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