Lithium hydroxide, monohydrate → HCID 71239142, compound

HRID 2171599Notes

Reaction equation

HRID 2171599 reaction equation
C([O:9][C@H:10]1[C@@H:17]2[N:13]([N:14]=[C:15]([C:20]3[CH:25]=[CH:24][C:23]([C:26]#[N:27])=[C:22]([Cl:28])[C:21]=3[CH3:29])[C@H:16]2[O:18][CH3:19])[CH2:12][CH2:11]1)(=O)C1C=CC=CC=1.O[Li].O>C1COCC1.O>[Cl:28][C:22]1[C:21]([CH3:29])=[C:20]([C:15]2[C@@H:16]([O:18][CH3:19])[C@@H:17]3[C@H:10]([OH:9])[CH2:11][CH2:12][N:13]3[N:14]=2)[CH:25]=[CH:24][C:23]=1[C:26]#[N:27]

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 71239485HCID 71239485, compound

Product 1

HCID 71239142HCID 71239142, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (3S,3aS,4R)-2-(3-chloro-4-cyano-2-methylphenyl)-3-methoxy-3a,4,5,6-tetrahydro-3H-pyrrolo[1,2-b]pyrazol-4-yl benzoate (80 mg, 0.0.195 mmol) in THF (2 mL) at 0° C. was added a solution of LiOH.H2O (25 mg, 0.586 mmol) in water and the reaction mixture was stirred at room temperature for overnight. Once the starting material had disappeared (monitored by TLC), reaction mixture was extracted with ethyl acetate. Organic layer was washed with saturated NaHCO3 solution, water, and brine and then dried over Na2SO4 and concentrated. Purification of the crude by column chromatography over silica gel using 2% MeOH in DCM provided the title compound.

Workup

  1. custom(monitored by TLC), reaction mixture
  2. extractionwas extracted with ethyl acetate
  3. washOrganic layer was washed with saturated NaHCO3 solution, water, and brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated
  6. customPurification of the crude by column chromatography over silica gel using 2% MeOH in DCM

Sources & evidence

ORD record
ord-22918d090b5346d2b6cfaf84613e50d7
Source dataset
uspto-grants-2015_06
Patent number
US09051326B2

Reaction notes

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