2-Phenylethanol → HCID 71060038, compound

HRID 337239Notes

Reaction equation

HRID 337239 reaction equation
[H-].[Na+].[CH2:3]([OH:11])[CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.[C:12]([O:16][C:17](=[O:35])[NH:18][CH:19]1[CH2:24][CH2:23][N:22]([S:25]([C:28]2[CH:29]=[N:30][C:31](Cl)=[CH:32][CH:33]=2)(=[O:27])=[O:26])[CH2:21][CH2:20]1)([CH3:15])([CH3:14])[CH3:13]>CN(C=O)C>[C:12]([O:16][C:17](=[O:35])[NH:18][CH:19]1[CH2:20][CH2:21][N:22]([S:25]([C:28]2[CH:29]=[N:30][C:31]([O:11][CH2:3][CH2:4][C:5]3[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=3)=[CH:32][CH:33]=2)(=[O:27])=[O:26])[CH2:23][CH2:24]1)([CH3:15])([CH3:13])[CH3:14]

Participants

5

Reactant 3

HCID 60542-PhenylethanolHCID 24758Sodium hydrideHCID 86674092HCID 86674092, compound

Product 1

HCID 71060038HCID 71060038, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

Sodium hydride (0.03 g, 1.15 mmol, 60% suspension in mineral oil) was added in portion wise to a cool (0° C.), stirred solution of phenethyl alcohol (0.08 g, 0.64 mmol) in DMF (5 ml) and the mixture was stirred at this temperature for 5 minutes. After this time, [1-(6-chloro-pyridine-3-sulfonyl)piperidin-4-yl]-carbamic acid tert-butyl ester (0.2 g, 0.5 mmol) was added in one portion and the mixture was warmed to room temperature stirred at this temperature under a nitrogen atmosphere for 12 hours. After this time the mixture was cooled to room temperature, concentrated and the resulting residue was diluted with DCM (50 ml) and washed sequentially with HCl (1M solution, 20 ml), NaOH (1M solution, 20 ml) and brine (20 ml). The organic layer was separated, dried (MgSO4), filtered and concentrated to give the title compound (0.18 g, 75% yield) as a white solid. Tr=2.32 min, m/z (ES+) (M+H)+ 462.

Workup

  1. temperaturethe mixture was warmed to room temperature
  2. stirringstirred at this temperature under a nitrogen atmosphere for 12 hours
  3. temperatureAfter this time the mixture was cooled to room temperature
  4. concentrationconcentrated
  5. additionthe resulting residue was diluted with DCM (50 ml)
  6. washwashed sequentially with HCl (1M solution, 20 ml), NaOH (1M solution, 20 ml) and brine (20 ml)
  7. customThe organic layer was separated
  8. dry with materialdried (MgSO4)
  9. filtrationfiltered
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-f0484b914a8e47418b59debcf7b78d01
Source dataset
uspto-grants-2014_11
Patent number
US08889716B2

Reaction notes

Loading…