Methyl p-toluenesulfonate → HCID 10270884, compound

HRID 411596Notes

Reaction equation

HRID 411596 reaction equation
COS([C:6]1[CH:11]=[CH:10][C:9](C)=[CH:8][CH:7]=1)(=O)=O.[NH:13]1[CH2:18][CH:17]=[C:16]([C:19]2[C:27]3[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=3)[NH:21][CH:20]=2)[CH2:15][CH2:14]1.[C:28](=[O:31])(O)[O-].[Na+].CN(C)[CH:35]=[O:36].[O:38]1[CH2:42][CH2:41]CC1>>[CH3:35][O:36][C:6]1[C:7]2[O:38][CH:42]([CH2:41][N:13]3[CH2:14][CH:15]=[C:16]([C:19]4[C:27]5[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=5)[NH:21][CH:20]=4)[CH2:17][CH2:18]3)[CH2:28][O:31][C:8]=2[CH:9]=[CH:10][CH:11]=1

Participants

5

Reactant 4

HCID 6645Methyl p-toluenesulfonateHCID 516892Sodium BicarbonateHCID 27610233-(1,2,3,6-Tetrahydropyridin-4-yl)-1H-indoleHCID 21974620tetrahydrofuran N,N-dimethylformamide

Product 1

HCID 10270884HCID 10270884, compound

Procedure

(2R)-8-Methoxy-2,3-dihydro-benzo[1,4]dioxin-2-yl]methyl-4-methylbenzenesulfonate (1.1 g, 3.1 mmole) was dissolved in a mixture of dimethylformamide/tetrahydrofuran (1:1 v/v, 50 mL) and 3-(1,2,3,6-tetrahydro-4-pyridinyl)-1H-indole (0.60 g 1.6 mmole) added, followed by sodium bicarbonate (1.0 g). The reaction mixture was refluxed under nitrogen for 18 hours, then cooled and concentrated in vacuum. The residue was partitioned between 400 mL each of water and ethyl acetate. The layers were separated. The organic phase was washed with water and saturated aqueous sodium chloride solution, dried over anhydrous potassium carbonate and evaporated to a foam (1.0 g). Trituration with ether yielded a solid which was recrystallized from boiling chloroform/methanol (1:1 v/v) to give 0.40 g (40%) of the (S)-enantiomer of the title compound as an off-white solid one-quarter hydrate, m.p. 203-205° C.

Workup

  1. additionadded
  2. temperatureThe reaction mixture was refluxed under nitrogen for 18 hours
  3. temperaturecooled
  4. concentrationconcentrated in vacuum
  5. customThe residue was partitioned between 400 mL each of water and ethyl acetate
  6. customThe layers were separated
  7. washThe organic phase was washed with water and saturated aqueous sodium chloride solution
  8. dry with materialdried over anhydrous potassium carbonate
  9. customevaporated to a foam (1.0 g)
  10. customTrituration with ether yielded a solid which
  11. customwas recrystallized

Sources & evidence

ORD record
ord-c0f0e8b5cc704938806f6a9d75dcd1b8
Source dataset
uspto-grants-2003_05
Patent number
US06559169B2

Reaction notes

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