HCID 68455295, compound → HCID 51357134, compound

HRID 2357640Notes

Reaction equation

HRID 2357640 reaction equation
[CH2:1]([N:8]([C@H:13]([CH3:16])[CH2:14][OH:15])[C:9](=[O:12])[CH2:10]Cl)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>C1COCC1.[H-].[Na+]>[CH2:1]([N:8]1[C@H:13]([CH3:16])[CH2:14][O:15][CH2:10][C:9]1=[O:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 1

HCID 68455295HCID 68455295, compound

Product 1

HCID 51357134HCID 51357134, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 24758Sodium hydrideSolvent

Procedure

(R)-N-Benzyl-2-chloro-N-(1-hydroxypropan-2-yl)acetamide (9.49 g, 39.3 mmol) was dissolved in THF (78.5 mL) before NaH—60% in oil (1.73 g, 43.2 mmol) was added and the mixture stirred at reflux for 4 h. The reaction was quenched with a few drops of water, concentrated, diluted with dichloromethane, filtered, and concentrated to give the title compound. MS (ES+): 206(M+H)+.

Workup

  1. additionwas added
  2. temperatureat reflux for 4 h
  3. customThe reaction was quenched with a few drops of water
  4. concentrationconcentrated
  5. additiondiluted with dichloromethane
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-70ad3f4d271f4c8cae38d92229cc81be
Source dataset
uspto-grants-2010_07
Patent number
US07759337B2

Reaction notes

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