Hydroxy azide → tert-butyl N-hydroxycarbamate
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
Product 1
Reagents, catalysts & solvents 2
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
- filtrationThe reaction mixture was filtered through a sintered glass funnel
- concentrationconcentrated on a rotary evaporator
- customThe residue was triturated with ether
- customthe solid was collected
- customdried
Sources & evidence
- ORD record
- ord-d1ffc1979063447796ecd1b9b595fed9
- Source dataset
- uspto-grants-2005_05
- Patent number
- US06890915B2
Reaction notes
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