Ammonia → HCID 68871447, compound

HRID 2108323Notes

Reaction equation

HRID 2108323 reaction equation
[Si:1]([O:8][CH:9]1[CH2:14][C:13](=[O:15])[O:12][C:11](=O)[CH2:10]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[OH-].[NH4+:18].N>O1CCOCC1>[Si:1]([O:8][CH:9]1[CH2:14][C:13](=[O:15])[NH:18][C:11](=[O:12])[CH2:10]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 222AmmoniaHCID 14923Ammonium HydroxideHCID 41410403-(tert-Butyldimethylsilyloxy)glutaric anhydride

Product 1

HCID 68871447HCID 68871447, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

Dissolve 4.1 mmol of 4-(tert-butyldimethylsilyloxy)dihydro-2H-pyran-2,6(3H)-dione (Nagao Y et al., Chem. Lett. 1990 9: 1503) in 10 mL of dioxane in a pressure tube. Cool in an ice/water bath, add 15 mL of saturated ammonium hydroxide and treat with gaseous ammonia via bubbler for about 10 min. Cap the pressure tube and heat in a 100° C. oil bath for 17 h. Cool the mixture and concentrate in vacuo. Purify the residue by silica gel chromatography using ethyl acetate/hexanes eluant to yield the title compound.

Workup

  1. temperatureCool in an ice/water bath
  2. customCap the pressure tube
  3. temperatureCool the mixture
  4. concentrationconcentrate in vacuo
  5. customPurify the residue by silica gel chromatography

Sources & evidence

ORD record
ord-e71af8df398141858e4518bc0f82dc60
Source dataset
uspto-grants-2009_04
Patent number
US07514068B2

Reaction notes

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