Methyl p-toluenesulfonate → HCID 10270884, compound

HRID 1823838Notes

Reaction equation

HRID 1823838 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-e9fbed5081f7439589fa90dbf3582bfa
Source dataset
uspto-grants-2006_05
Patent number
US07041683B2

Reaction notes

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