Lithium hydroxide, monohydrate → HCID 86713331, compound

HRID 928002Notes

Reaction equation

HRID 928002 reaction equation
[NH2:1][C:2]1[C:11]([C:12]([O:14]C)=[O:13])=[C:10]2[C:5]([CH:6]3[CH2:16][CH:7]3[CH2:8][O:9]2)=[CH:4][CH:3]=1.O.[OH-].[Li+]>O1CCOCC1.O>[NH2:1][C:2]1[C:11]([C:12]([OH:14])=[O:13])=[C:10]2[C:5]([CH:6]3[CH2:16][CH:7]3[CH2:8][O:9]2)=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 86713293Methyl 5-amino-1,1a,2,7b-tetrahydrocyclopropa[c]chromene-4-carboxylate2×

Product 1

HCID 86713331HCID 86713331, compoundYield 103.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of methyl (1aRS,7bSR)-5-amino-1,1a,2,7b-tetrahydrocyclopropa[c]chromene-4-carboxylate (Intermediate 42, 1.0 g) and lithium hydroxide monohydrate (0.96 g) in dioxane (16 mL) and water (14 mL) was stirred and heated at 90° C. for 1 hour. After cooling, the mixture was concentrated under vacuum and the residue was diluted with water and neutralised to pH7 with formic acid. The mixture was then extracted with ethyl acetate, dried (Na2SO4) and filtered and the filtrate was evaporated to dryness to give (1aRS,7bSR)-5-amino-1,1a,2,7b-tetrahydro-cyclopropa-[c]chromene-4-carboxylic acid (0.97 g) as a yellow oil.

Workup

  1. temperatureAfter cooling
  2. concentrationthe mixture was concentrated under vacuum
  3. additionthe residue was diluted with water and neutralised to pH7 with formic acid
  4. extractionThe mixture was then extracted with ethyl acetate
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. customthe filtrate was evaporated to dryness

Sources & evidence

ORD record
ord-ff7d7f0c85dd4b46aafd76b4ce16d5d4
Source dataset
uspto-grants-2016_03
Patent number
US09290472B2

Reaction notes

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