Lithium hydroxide, monohydrate → HCID 23627747, compound

HRID 1887215Notes

Reaction equation

HRID 1887215 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 (Example 57) (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, 0.858 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 product. The precipitate was then triturated with water (2×5 mL) and dried under a stream of nitrogen to afford product as a colorless solid (318 mg, 96%). 1H NMR (CDCl3) 1.43-1.57 (m, 2 H), 1.77-1.79 (m, 6 H), 3.02-3.15 (m, 2 H), 3.27 (br s, 2 H), 3.51 (br s, 1 H), 3.74 (s, 3 H), 3.77-3.89 (m, 2 H), 4.57-4.59 (m, 1 H), 6.24-6.31 (m, 2 H), 6.55 (br s, OH), 6.67 (d, J=8.6, 1 H)7.18-7.27 (m, 5 H). LC/MS 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 product
  4. customThe precipitate was then triturated with water (2×5 mL)
  5. customdried under a stream of nitrogen

Sources & evidence

ORD record
ord-bb7116917ed3425fbfd5b671f070e9bb
Source dataset
uspto-grants-2013_08
Patent number
US08501745B2

Reaction notes

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