Methyl iodide → N-[(1R,2R)-2-(tert-butyl-dimethyl-silanyloxy)-indan-1-yl]-N-methyl-methanesulphonamide

HRID 1258170Notes

Reaction equation

HRID 1258170 reaction equation
[C:1]([Si:5]([CH3:22])([CH3:21])[O:6][C@@H:7]1[CH2:15][C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[C@H:8]1[NH:16][S:17]([CH3:20])(=[O:19])=[O:18])([CH3:4])([CH3:3])[CH3:2].[C:23]([O-])([O-])=O.[Cs+].[Cs+].CI.[OH-].[Na+]>CN(C=O)C.C(Cl)Cl>[C:1]([Si:5]([CH3:22])([CH3:21])[O:6][C@@H:7]1[CH2:15][C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[C@H:8]1[N:16]([CH3:23])[S:17]([CH3:20])(=[O:19])=[O:18])([CH3:4])([CH3:3])[CH3:2]

Participants

7

Reactant 4

HCID 6328Methyl iodideHCID 10796Cesium carbonateHCID 14798Sodium HydroxideHCID 58450866N-[(1R,2R)-2-(tert-butyl-dimethyl-silanyloxy)-indan-1-yl]-methanesulphonamide

Product 1

HCID 58450838N-[(1R,2R)-2-(tert-butyl-dimethyl-silanyloxy)-indan-1-yl]-N-methyl-methanesulphonamide

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

N-[(1R,2R)-2-(tert-butyl-dimethyl-silanyloxy)-indan-1-yl]-methanesulphonamide (0.50 g) is dissolved in 2 mL DMF and mixed with Cs2CO3 (0.96 g, 2.93 mmol) and MeI (0.10 mL). The reaction mixture is stirred for 2 h and, once the reaction has ended, combined with DCM and NaOH (1 N). The organic phase is dried on MgSO4 and freed from the solvent using the rotary evaporator. After dissolving in acetonitrile water is added. The precipitate formed is filtered off, washed with water and taken up in DCM. After drying on MgSO4 the solvent is eliminated using the rotary evaporator.

Workup

  1. customThe organic phase is dried on MgSO4
  2. customthe rotary evaporator
  3. dissolutionAfter dissolving in acetonitrile water
  4. additionis added
  5. customThe precipitate formed
  6. filtrationis filtered off
  7. washwashed with water
  8. customAfter drying on MgSO4 the solvent
  9. customthe rotary evaporator

Sources & evidence

ORD record
ord-d090893ec286428fa87a90e23598adc9
Source dataset
uspto-grants-2013_06
Patent number
US08466155B2

Reaction notes

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