Lithium hydroxide, monohydrate → HCID 71239171, compound

HRID 2171602Notes

Reaction equation

HRID 2171602 reaction equation
C([O:9][C@H:10]1[C@@H:17]2[N:13]([N:14]=[C:15]([C:25]3[CH:30]=[CH:29][C:28]([C:31]#[N:32])=[C:27]([Cl:33])[C:26]=3[CH3:34])[C@H:16]2[O:18][CH:19]2[CH2:24][CH2:23][CH2:22][CH2:21][O:20]2)[CH2:12][CH2:11]1)(=O)C1C=CC=CC=1.O[Li].O>C1COCC1.O>[Cl:33][C:27]1[C:26]([CH3:34])=[C:25]([C:15]2[C@@H:16]([O:18][CH:19]3[CH2:24][CH2:23][CH2:22][CH2:21][O:20]3)[C@@H:17]3[C@H:10]([OH:9])[CH2:11][CH2:12][N:13]3[N:14]=2)[CH:30]=[CH:29][C:28]=1[C:31]#[N:32]

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 71239236HCID 71239236, compound

Product 1

HCID 71239171HCID 71239171, compoundYield 90%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (3S,3aS,4R)-2-(3-chloro-4-cyano-2-methylphenyl)-3-(tetrahydro-2H-pyran-2-yloxy)-3a,4,5,6-tetrahydro-3H-pyrrolo[1,2-b]pyrazol-4-yl benzoate (100 mg, 0.208 mmol) in THF (2 mL) at 0° C. was added a solution of LiOH.H2O (25 mg, 0.586 mmol) in water (1 mL) 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 water and brine then dried over Na2SO4 and concentrated to get the crude product which was used in the next step without further purification.

Workup

  1. custom(monitored by TLC), reaction mixture
  2. extractionwas extracted with ethyl acetate
  3. washOrganic layer was washed with water and brine
  4. dry with materialthen dried over Na2SO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-564ee036e4214cb88c691730f613d905
Source dataset
uspto-grants-2015_06
Patent number
US09051326B2

Reaction notes

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