Butyl iodide → N--t-Butoxycarbonyl-N-butyl-O-benzylhydroxylamine

HRID 383148

Reaction equation

HRID 383148 reaction equation
[C:1]([O:5][C:6]([NH:8][O:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].I[CH2:20][CH2:21][CH2:22][CH3:23]>C1COCC1>[C:1]([O:5][C:6]([N:8]([CH2:20][CH2:21][CH2:22][CH3:23])[O:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 10962Butyl iodideHCID 24758Sodium hydrideHCID 736159Tert-butyl N-(benzyloxy)carbamate

Product 1

HCID 53942485N--t-Butoxycarbonyl-N-butyl-O-benzylhydroxylamine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution at 0° C. of N--t-Butoxycarbonyl-O-benzylhydroxylamine, prepared as in Example 1175A, in anhydrous THF was added portionwise a 60% dispersion of sodium hydride (1.2 equiv.) in mineral oil. Mixture stirred 30 minutes ar 0° C., and then, 1-iodobutane (1.2 equiv.) was added dropwise. Reaction stirred one hour at 0° C., and than, overnight at room temperature. Reaction concentrated in vacuo. Residue taken up in EtOAc and washed with water, 1.0M NaHCO3, 1N H3PO4, and brine. Organic layer dried with Na2SO4, filtered, and evaporated.

Workup

  1. customar 0° C.
  2. customReaction
  3. stirringstirred one hour at 0° C.
  4. customovernight
  5. customat room temperature
  6. customReaction
  7. concentrationconcentrated in vacuo
  8. washwashed with water, 1.0M NaHCO3, 1N H3PO4, and brine
  9. dry with materialOrganic layer dried with Na2SO4
  10. filtrationfiltered
  11. customevaporated

Sources & evidence

ORD record
ord-7cff57209b0a4774829073d5d421076a
Source dataset
uspto-grants-2001_10
Patent number
US06310095B1

Linked notes

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