tert-butyl (2S,4S,5S)-5-azido-2-methyltetrahydro-2H-pyran-4-ylcarbamate → HCID 118043450, compound

HRID 56446Notes

Reaction equation

HRID 56446 reaction equation
[N:1]([C@@H:4]1[CH2:9][O:8][C@@H:7]([CH3:10])[CH2:6][C@@H:5]1[NH:11][C:12](=[O:18])[O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[N+]=[N-]>[Pd].C(O)(C)C>[NH2:1][C@@H:4]1[CH2:9][O:8][C@@H:7]([CH3:10])[CH2:6][C@@H:5]1[NH:11][C:12](=[O:18])[O:13][C:14]([CH3:17])([CH3:16])[CH3:15]

Participants

4

Reactant 1

HCID 118043452tert-butyl (2S,4S,5S)-5-azido-2-methyltetrahydro-2H-pyran-4-ylcarbamate

Product 1

HCID 118043450HCID 118043450, compoundYield 18.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 3776IsopropanolSolvent

Procedure

A mixture of tert-butyl (2S,4S,5S)-5-azido-2-methyltetrahydro-2H-pyran-4-ylcarbamate (1.8 g, 3.6 mmol) and 10% palladium on carbon (50 mg) in isopropanol (10 mL) was stirred at room temperature under hydrogenation overnight. After that, the mixture was filtered through a pad of celite. Concentrated to get the title compound (150 mg, crude) as a yellow oil, which was used directly for the next step without further purification.

Workup

  1. filtrationAfter that, the mixture was filtered through a pad of celite
  2. concentrationConcentrated

Sources & evidence

ORD record
ord-e3830da5723f4069a320a05e18ed562b
Source dataset
uspto-grants-2016_09
Patent number
US09434700B2

Reaction notes

Loading…