Sodium Hydroxide → Aplindore

HRID 1259465Notes

Reaction equation

HRID 1259465 reaction equation
CC1C=CC(S(O)(=O)=O)=CC=1.[CH2:12]([NH:19][CH2:20][C@@H:21]1[O:34][C:25]2=[C:26]3[C:30](=[CH:31][CH:32]=[C:24]2[O:23][CH2:22]1)[NH:29][C:28](=[O:33])[CH2:27]3)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[OH-].[Na+]>CC1CCCO1.C(O)C>[CH2:12]([NH:19][CH2:20][C@@H:21]1[O:34][C:25]2=[C:26]3[C:30](=[CH:31][CH:32]=[C:24]2[O:23][CH2:22]1)[NH:29][C:28](=[O:33])[CH2:27]3)[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 86644796(2S)-2-[(benzylamino)methyl]-2,3,8,9-tetrahydro-7H-[1,4]dioxino[2,3-e]indol-8-one 4-methylbenzenesulfonate

Product 1

HCID 158784Aplindore

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 73012-MethyltetrahydrofuranSolvent

Procedure

(2S)-2-[(benzylamino)methyl]-2,3,8,9-tetrahydro-7H-[1,4]dioxino[2,3-e]indol-8-one 4-methylbenzenesulfonate (0.75 g, 1.54 mmol) is suspended in 2-methyl tetrahydrofuran (10 mL), 1 N NaOH is added until the solids dissolve and the pH of the aqueous phase is 10 (pH paper), about 1.6 mL is required. The aqueous layer is removed, and the organic phase is washed with water (2×2 mL). The volatiles are removed by rotary evaporation to give a yellow syrup. The syrup is dissolved in absolute ethanol (3 mL) and evaporated to dryness. Absolute ethanol (3 mL) is added to the residue and removed by rotary evaporation to give crude (2S)-2-[(benzylamino)methyl]-2,3,8,9-tetrahydro-7H-[1,4]dioxino[2,3-e]indol-8-one as a yellow syrup which is carried directly into the next step.

Workup

  1. dissolutiondissolve
  2. customThe aqueous layer is removed
  3. washthe organic phase is washed with water (2×2 mL)
  4. customThe volatiles are removed by rotary evaporation
  5. customto give a yellow syrup
  6. customevaporated to dryness
  7. additionAbsolute ethanol (3 mL) is added to the residue
  8. customremoved by rotary evaporation

Sources & evidence

ORD record
ord-d1c28b74ba064829bfe2662c34530531
Source dataset
uspto-grants-2013_06
Patent number
US08466296B2

Reaction notes

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