Hydroxylamine → tert-butyl N-hydroxycarbamate

HRID 332131Notes

Reaction equation

HRID 332131 reaction equation
[CH3:1][C:2]([O:5][C:6]([O:8]C(OC(C)(C)C)=O)=O)([CH3:4])[CH3:3].[NH2:16][OH:17].O>C(Cl)Cl>[C:6]([NH:16][OH:17])([O:5][C:2]([CH3:4])([CH3:3])[CH3:1])=[O:8]

Participants

5

Reactant 3

HCID 787HydroxylamineHCID 962WaterHCID 90495Di-tert-butyl dicarbonate

Product 1

HCID 97534tert-butyl N-hydroxycarbamate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Boc anhydride (5.91 g, 0.026 mole) was added in one portion to a stirred solution of amino alcohol in anhydrous DCM (150 mL), and the reaction mixture stirred at ambient temperature under argon for 4.5 h. Water (200 mL) was added to the reaction mixture and the organic layer separated. The organic layer was washed with brine (100 mL), dried (Na2SO4), filtered, and concentrated to give N-boc amino alcohol as a colorless liquid that became a colorless glass upon standing. The material was used without further purification. Yield: 9.0 g (quantitative); LCMS: (+) ESI: m/z=368 [M+Na]+.

Workup

  1. customthe organic layer separated
  2. washThe organic layer was washed with brine (100 mL)
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-d23af64ae58241b38edb8414f2c41ae4
Source dataset
uspto-grants-2014_11
Patent number
US08877798B2

Reaction notes

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