{[(2S)-2-azido-2-tetrahydro-2H-pyran-4-ylethyl]oxy}(tert-butyl)dimethylsilane → (1S)-2-{[tert-butyl(dimethyl)silyl]oxy}-1-tetrahydro-2H-pyran-4-ylethanamine

HRID 221593Notes

Reaction equation

HRID 221593 reaction equation
[N:1]([C@@H:4]([CH:14]1[CH2:19][CH2:18][O:17][CH2:16][CH2:15]1)[CH2:5][O:6][Si:7]([C:10]([CH3:13])([CH3:12])[CH3:11])([CH3:9])[CH3:8])=[N+]=[N-]>CO.[Pd]>[Si:7]([O:6][CH2:5][C@H:4]([CH:14]1[CH2:15][CH2:16][O:17][CH2:18][CH2:19]1)[NH2:1])([C:10]([CH3:13])([CH3:12])[CH3:11])([CH3:9])[CH3:8]

Participants

4

Reactant 1

HCID 86624126{[(2S)-2-azido-2-tetrahydro-2H-pyran-4-ylethyl]oxy}(tert-butyl)dimethylsilane

Product 1

HCID 67156857(1S)-2-{[tert-butyl(dimethyl)silyl]oxy}-1-tetrahydro-2H-pyran-4-ylethanamineYield 97.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

{[(2S)-2-Azido-2-tetrahydro-2H-pyran-4-ylethyl]oxy}(tert-butyl)dimethylsilane (2.19 g, 7.68 mmol) was dissolved in 25 mL of methanol and the solution was placed in a pressure bottle. Palladium on carbon (10%, 250 mg) was then added and the reaction mixture was shaken under H2 at 50 PSI (3.4×105 Pa). After 18 hours, the reaction mixture was filtered through a pad of CELITE filter agent. The pad was rinsed with methanol and the combined filtrates were concentrated under reduced pressure to give 1.94 g of (1S)-2-{[tert-butyl(dimethyl)silyl]oxy}-1-tetrahydro-2H-pyran-4-ylethanamine as a colorless syrup.

Workup

  1. filtrationthe reaction mixture was filtered through a pad of CELITE
  2. filtrationfilter agent
  3. washThe pad was rinsed with methanol
  4. concentrationthe combined filtrates were concentrated under reduced pressure

Sources & evidence

ORD record
ord-5922523dce6e4ee0a570d3bb3d35a670
Source dataset
uspto-grants-2012_06
Patent number
US08207162B2

Reaction notes

Loading…