Water → tert-Butyl [(1S)-1-methyl-2-(pyridin-4-yloxy)ethyl]carbamate

HRID 2368058Notes

Reaction equation

HRID 2368058 reaction equation
[H-].[Na+].[OH:3][C:4]1[CH:9]=[CH:8][N:7]=[CH:6][CH:5]=1.CC1C=CC(S(O[CH2:21][C@@H:22]([NH:24][C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[CH3:23])(=O)=O)=CC=1.O>CN(C=O)C>[CH3:23][C@H:22]([NH:24][C:25](=[O:26])[O:27][C:28]([CH3:29])([CH3:31])[CH3:30])[CH2:21][O:3][C:4]1[CH:9]=[CH:8][N:7]=[CH:6][CH:5]=1

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 13200311(S)-2-((tert-butoxycarbonyl)amino)propyl 4-methylbenzenesulfonateHCID 178418642HCID 178418642, compound

Product 1

HCID 57517478tert-Butyl [(1S)-1-methyl-2-(pyridin-4-yloxy)ethyl]carbamateYield 20.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a suspension of sodium hydride (oil, 60%, 1.61 g) in DMF (50 mL) was added 4-hydroxypyridine (3.83 g) under ice-cooling. The reaction mixture was stirred for 30 min under ice-cooling, and (2S)-2-[(tert-butoxycarbonyl)amino]propyl 4-methylbenzenesulfonate (13.3 g) was added thereto in small portions under ice-cooling. The reaction mixture was stirred for 2 hr under ice-cooling, and at 60° C. for 3 hr. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The obtained organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure and the residue was purified by silica gel column chromatography (hexane/ethyl acetate) to give the title compound (2.10 g).

Workup

  1. temperaturecooling
  2. temperaturecooling
  3. temperaturein small portions under ice-cooling
  4. stirringThe reaction mixture was stirred for 2 hr under ice-
  5. temperaturecooling
  6. waitat 60° C. for 3 hr
  7. extractionthe mixture was extracted with ethyl acetate
  8. washThe obtained organic layer was washed with saturated brine
  9. dry with materialdried over anhydrous magnesium sulfate
  10. customThe solvent was evaporated under reduced pressure
  11. customthe residue was purified by silica gel column chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-48c3b04b55f444838f6783b89dbd48f3
Source dataset
uspto-grants-2014_04
Patent number
US08703758B2

Reaction notes

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