trans-(4-Azido-tetrahydro-pyran-3-yl)-carbamic acid tert-butyl ester → tert-Butyl ((3S,4R)-4-aminotetrahydro-2H-pyran-3-yl)carbamate

HRID 39420Notes

Reaction equation

HRID 39420 reaction equation
[C:1]([O:5][C:6](=[O:17])[NH:7][C@H:8]1[C@H:13]([N:14]=[N+]=[N-])[CH2:12][CH2:11][O:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2]>CO.[Pt](=O)=O>[C:1]([O:5][C:6](=[O:17])[NH:7][C@H:8]1[C@H:13]([NH2:14])[CH2:12][CH2:11][O:10][CH2:9]1)([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 1

HCID 86656338trans-(4-Azido-tetrahydro-pyran-3-yl)-carbamic acid tert-butyl ester2×

Product 1

HCID 67358958tert-Butyl ((3S,4R)-4-aminotetrahydro-2H-pyran-3-yl)carbamate

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 887MethanolSolvent

Procedure

trans-(4-Azido-tetrahydro-pyran-3-yl)-carbamic acid tert-butyl ester (intermediate F) (3.3 g, 14 mmol) was dissolved in 27 mL methanol. Platinum (IV) oxide (307 mg, 1.4 mmol) was added was the reaction mixture was hydrogenated with a H2-balloon at room temperature overnight. The catalyst was filtered off and the solvent was evaporated off. The crude material, off-white solid (2.74 g, 93%), MS: m/e=161 [(M-buten)+] was used without further purification.

Workup

  1. filtrationThe catalyst was filtered off
  2. customthe solvent was evaporated off
  3. customThe crude material, off-white solid (2.74 g, 93%), MS: m/e=161 [(M-buten)+] was used without further purification

Sources & evidence

ORD record
ord-669f751ad8094a889e4bd716d10e854d
Source dataset
uspto-grants-2013_09
Patent number
US08524909B2

Reaction notes

Loading…