Lithium hydroxide, monohydrate → HCID 42641990, compound

HRID 2382206Notes

Reaction equation

HRID 2382206 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([N:14]3[CH2:19][CH2:18][N:17]([CH2:20][C:21]([O:23]C)=[O:22])[C@H:16]([CH3:25])[CH2:15]3)[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]2)=[CH:4][CH:3]=1.O[Li].O>C1COCC1.CO.O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([N:14]3[CH2:19][CH2:18][N:17]([CH2:20][C:21]([OH:23])=[O:22])[C@H:16]([CH3:25])[CH2:15]3)[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]2)=[CH:4][CH:3]=1

Participants

6

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 68769376HCID 68769376, compound

Product 1

HCID 42641990HCID 42641990, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (R)-methyl 2-(4-(1-(4-chlorophenyl)cyclohexyl)-2-methyl-piperazin-1-yl)acetate (0.5 g, 1.37 mmol) in THF (10 mL) and methanol (1 mL) at 0° C. was added a solution of LiOH.H2O (0.16 g, 3.81 mmol) in water (1 mL). The reaction mixture was stirred for 4 h. Methanol and THF were distilled under reduced pressure and the residue was washed with ethyl acetate. The pH of the aqueous layer was adjusted to 7 and extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure to afford the crude product which was purified by silica gel (100-200 mesh) column chromatography eluting with 5-7% methanol in chloroform to afford pure (R)-2-(4-(1-(4-chlorophenyl)cyclohexyl)-2-methylpiperazin-1-yl)acetic acid.

Workup

  1. distillationMethanol and THF were distilled under reduced pressure
  2. washthe residue was washed with ethyl acetate
  3. extractionextracted with ethyl acetate
  4. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customto afford the crude product which
  7. customwas purified by silica gel (100-200 mesh) column chromatography
  8. washeluting with 5-7% methanol in chloroform

Sources & evidence

ORD record
ord-4379b15e55eb4d39986f4745d186b08c
Source dataset
uspto-grants-2012_09
Patent number
US08258306B2

Reaction notes

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