Methyl iodide → ethyl 3-(N-benzyloxycarbonyl-N-methylamino)propionate

HRID 276927

Reaction equation

HRID 276927 reaction equation
[H-].[Na+].[CH2:3]([O:10][C:11]([NH:13][CH2:14][CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17])=[O:12])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[CH3:21]I>O1CCCC1.CN(C)C=O.O.CCCCCC.C(OCC)(=O)C>[CH2:3]([O:10][C:11]([N:13]([CH2:14][CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17])[CH3:21])=[O:12])[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Participants

9

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 12116647Ethyl 3-{[(benzyloxy)carbonyl]amino}propanoate

Product 1

HCID 22629164ethyl 3-(N-benzyloxycarbonyl-N-methylamino)propionate

Reagents, catalysts & solvents 5

HCID 962WaterSolvent2×HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolventHCID 8058HexaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a suspension of sodium hydride (1.92 g, 60% in Oil) in a mixture of tetrahydrofuran (200 ml) and N,N-dimethylformamide (50 ml) was added dropwise ethyl 3-(benzyloxycarbonylamino)propionate (10 g) at 30° C. under nitrogen atmosphere, which was stirred for 30 minutes. To the reaction mixture was added methyl iodide (3 ml) and stirred for additional 6 hours. To the resulting mixture was added carefully water (5 ml), which was poured into a mixture of ethyl acetate (500 ml), n-hexane (150 ml) and water (100 ml). Organic layer was separated, washed n turn with water (100 ml×3), 1N-aqueous hydrochloric acid (100 ml), brine (100 ml), saturated sodium hydrogen carbonate in water (100 ml) and brine (100 ml×2), and dried over magnesium sulfate. Evaporation of the solvent gave a residue, which was chromatographed on silica gel (250 ml) eluting In turn with n-hexane, 10%, 50% ethyl acetate in n-hexane to give ethyl 3-(N-benzyloxycarbonyl-N-methylamino)propionate (8.32 g).

Workup

  1. stirringstirred for additional 6 hours
  2. customOrganic layer was separated
  3. washwashed n
  4. dry with materialdried over magnesium sulfate
  5. customEvaporation of the solvent
  6. customgave a residue, which
  7. customwas chromatographed on silica gel (250 ml)
  8. washeluting In turn with n-hexane, 10%, 50% ethyl acetate in n-hexane

Sources & evidence

ORD record
ord-f8f8417a60574eba8804a1d637d1ce3d
Source dataset
uspto-grants-2002_03
Patent number
US06355640B1

Linked notes

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