Sodium hydride → HCID 57015382, compound

HRID 1374980Notes

Reaction equation

HRID 1374980 reaction equation
[CH2:1]([N:8]([CH2:13][C@H:14]([OH:18])[CH2:15][O:16][CH3:17])[C@@H:9]([CH3:12])[CH2:10]Cl)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+]>CN(C)C=O>[CH2:1]([N:8]1[C@@H:9]([CH3:12])[CH2:10][O:18][C@H:14]([CH2:15][O:16][CH3:17])[CH2:13]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 24758Sodium hydrideHCID 69419667HCID 69419667, compound

Product 1

HCID 57015382HCID 57015382, compoundYield 52.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A solution of (2S)-1-[N-benzyl-N-[(1S)-2-chloro-1-methylethyl]amino]-3-methoxy-2-propanol (1.90 g) in N,N-dimethylformamide (10 ml) was added to an ice-cooled suspension of sodium hydride (0.45 g, 60% in mineral oil) in N,N-dimethylformamide (10 ml) at 0° C. After being stirred for 1 hour at the same temperature, the mixture was poured into ice-water and extracted with ethyl acetate. The extract was washed with brine, dried over magnesium sulfate and evaporated under reduced pressure. The residue was purified is by column chromatography on silica gel using mixed solvents of hexane and ethyl acetate (10:1). The fractions containing the objective compound were collected and evaporated under reduced pressure to give (2S,5S)-4-benzyl-2-methoxymethyl-5-methylmorpholine (0.86 g) as an oil.

Workup

  1. temperaturecooled
  2. extractionextracted with ethyl acetate
  3. washThe extract was washed with brine
  4. dry with materialdried over magnesium sulfate
  5. customevaporated under reduced pressure
  6. customThe residue was purified
  7. additionmixed solvents of hexane and ethyl acetate (10:1)
  8. additionThe fractions containing the objective compound
  9. customwere collected
  10. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-7486644067c24de48f1f46d4cc9e7a16
Source dataset
uspto-grants-2007_01
Patent number
US07166598B2

Reaction notes

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