Hydroxylamine → tert-butyl N-hydroxycarbamate

HRID 1047510Notes

Reaction equation

HRID 1047510 reaction equation
[NH2:1][OH:2].C(N(CC)CC)C.[C:10]([O:14][C:15]([O:17]C([O-])=O)=O)([CH3:13])([CH3:12])[CH3:11]>C(Cl)Cl>[C:15]([NH:1][OH:2])([O:14][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:17]

Participants

5

Reactant 3

HCID 787HydroxylamineHCID 8471TriethylamineHCID 22064466Tert-butyldicarbonate

Product 1

HCID 97534tert-butyl N-hydroxycarbamateYield 362%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of amino alcohol from Step 3 (2.60 g, 5.81 mmol) in DCM (60 mL) was added triethylamine (1.60 mL, 12.0 mmol) followed by tert-butyldicarbonate (1.50 g, 6.88 mmol) and the reaction was stirred overnight at RT. The final mixture was concentrated and purified by flash-chromatography over silica gel (eluted with Hexanes/AcOEt 80:20 to 20:80) to provide 2.80 g (88%) of Boc-amino alcohol.

Workup

  1. concentrationThe final mixture was concentrated
  2. custompurified by flash-chromatography over silica gel (eluted with Hexanes/AcOEt 80:20 to 20:80)

Sources & evidence

ORD record
ord-9e32a710b1344846a049131a7fab3f87
Source dataset
uspto-grants-2013_10
Patent number
US08569521B2

Reaction notes

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