Lithium hydroxide, monohydrate → HCID 23627747, compound

HRID 1423125Notes

Reaction equation

HRID 1423125 reaction equation
C[O:2][C:3](=[O:32])[CH2:4][N:5]1[CH2:10][CH2:9][N:8]([C:11]2[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[C:13]([O:19][CH:20]3[CH2:24][CH2:23][CH2:22][CH2:21]3)[CH:12]=2)[CH2:7][C@@H:6]1[CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.O.[OH-].[Li+]>C1COCC1>[CH2:25]([C@H:6]1[CH2:7][N:8]([C:11]2[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[C:13]([O:19][CH:20]3[CH2:24][CH2:23][CH2:22][CH2:21]3)[CH:12]=2)[CH2:9][CH2:10][N:5]1[CH2:4][C:3]([OH:32])=[O:2])[C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1

Participants

4

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 23627745HCID 23627745, compound

Product 1

HCID 23627747HCID 23627747, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of [(S)-2-Benzyl-4-(3-cyclopentyloxy-4-methoxy-phenyl)-piperazin-1-yl]-acetic acid methyl ester (342 mg, 0.78 mmol) in THF (5 mL) at room temperature was treated with an aqueous solution (1 mL) containing lithium hydroxide monohydrate (36 mg, 0.86 mmol). The reaction mixture was allowed to stir for 2 h and then evaporated to a small volume. The reaction mixture was then dissolved in water (5 mL) and the pH adjusted to ˜7 with 1 N HCl to precipitate a solid. The precipitate was then triturated with water (2×5 mL) and dried under a stream of nitrogen to afford the title compound as a colorless solid (318 mg, 96%). 1H NMR (CDCl3) 7.27-7.18 (m, 5H), 6.67 (d, J=8.6, 1H), 6.55 (br s, OH), 6.31-6.24 (m, 2H), 4.59-4.57 (m, 1H), 3.89-3.77 (m, 2H), 3.74 (s, 3H), 3.51 (br s, 2H), 3.27 (br s, 3H), 3.15-3.02 (m, 3H), 1.79-1.77 (m, 6H), 1.57-1.43 (m, 2H). LC/MS (Method A) 5.34 min, [M+1]+ 425.

Workup

  1. customevaporated to a small volume
  2. dissolutionThe reaction mixture was then dissolved in water (5 mL)
  3. customto precipitate a solid
  4. customThe precipitate was then triturated with water (2×5 mL)
  5. customdried under a stream of nitrogen

Sources & evidence

ORD record
ord-5729f04d6d474ca29ba14939c365f0ad
Source dataset
uspto-grants-2015_01
Patent number
US08927546B2

Reaction notes

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