Sodium hydride → (5R,6R)-4-benzyl-5-ethyl-6-methylmorpholin-3-one

HRID 81160Notes

Reaction equation

HRID 81160 reaction equation
[CH2:1]([N:8]([C@H:13]([CH2:17][CH3:18])[C@H:14]([OH:16])[CH3:15])[C:9](=[O:12])[CH2:10]Cl)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+]>C1COCC1>[CH2:1]([N:8]1[C@H:13]([CH2:17][CH3:18])[C@@H:14]([CH3:15])[O:16][CH2:10][C:9]1=[O:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 24758Sodium hydrideHCID 86724513N-benzyl-2-chloro-N-((2R,3R)-2-hydroxypentan-3-yl)acetamide

Product 1

HCID 86724515(5R,6R)-4-benzyl-5-ethyl-6-methylmorpholin-3-one

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

A solution of N-benzyl-2-chloro-N-((2R,3R)-2-hydroxypentan-3-yl)acetamide (210 mg, 0.7 mmol) in THF (5 mL) was added to a suspension of NaH (89 mg, 3.7 mmol) in THF (5 mL) at 0° C. The reaction mixture was stirred at 0° C. for 1 hour and then quenched with saturated NH4Cl solution. The layers were separated and the aqueous layer was extracted with EtOAc (2×10 mL). The combined organic layers were washed with brine, dried over anhydrous Na2SO4, filtered and concentrated in vacuo. Purification of the residue on a silica gel column (0 to 50% EtOAc/hexanes) afforded (5R,6R)-4-benzyl-5-ethyl-6-methylmorpholin-3-one. MS APCl calc'd for C14H19NO2 [M+H]+ 234. found 234.

Workup

  1. customquenched with saturated NH4Cl solution
  2. customThe layers were separated
  3. extractionthe aqueous layer was extracted with EtOAc (2×10 mL)
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried over anhydrous Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customPurification of the residue on a silica gel column (0 to 50% EtOAc/hexanes)

Sources & evidence

ORD record
ord-50bc3f91e9504640a225aa39a785b91e
Source dataset
uspto-grants-2014_09
Patent number
US08846657B2

Reaction notes

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