Hydroxy azide → tert-butyl N-hydroxycarbamate

HRID 1071370Notes

Reaction equation

HRID 1071370 reaction equation
[N:1]([OH:4])=[N+]=[N-].[C:5]([O:9][C:10](OC([O-])=O)=[O:11])([CH3:8])([CH3:7])[CH3:6]>CO.[OH-].[OH-].[Pd+2]>[C:10]([NH:1][OH:4])([O:9][C:5]([CH3:8])([CH3:7])[CH3:6])=[O:11]

Participants

5

Reactant 2

HCID 18670949Hydroxy azideHCID 22064466Tert-butyldicarbonate

Product 1

HCID 97534tert-butyl N-hydroxycarbamateYield 39.2%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

A solution of 15a (9.85 g, 69.8 mmol) and t-butyldicarbonate (18.3 g, 83.8 mmol) in 50 mL of MeOH was placed in a Parr bottle with 20% Pd(OH)2 (2.0 g) and hydrogenated under 50 psi of H2 overnight. The reaction mixture was filtered through a sintered glass funnel and concentrated on a rotary evaporator. The residue was triturated with ether and the solid was collected and dried to give 3.64 g (24% yield) of Boc-amino alcohol 15b.

Workup

  1. filtrationThe reaction mixture was filtered through a sintered glass funnel
  2. concentrationconcentrated on a rotary evaporator
  3. customThe residue was triturated with ether
  4. customthe solid was collected
  5. customdried

Sources & evidence

ORD record
ord-7d661687e19846aaab95f206782084cf
Source dataset
uspto-grants-2005_06
Patent number
US06906053B2

Reaction notes

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