Pyridine → Tert-butyl 6-{amino[({[(2-ethylhexyl)oxy]carbonyl}oxy)-imino]methyl}-4-{[tert-butyl(dimethyl)silyl]oxy}spiro[chroman-2,4'-piperidine]-1'-carboxylate

HRID 1096924Notes

Reaction equation

HRID 1096924 reaction equation
[NH2:1][C:2](=[N:33][OH:34])[C:3]1[CH:4]=[C:5]2[C:22](=[CH:23][CH:24]=1)[O:21][C:8]1([CH2:13][CH2:12][N:11]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:10][CH2:9]1)[CH2:7][CH:6]2[O:25][Si:26]([C:29]([CH3:32])([CH3:31])[CH3:30])([CH3:28])[CH3:27].N1C=CC=CC=1.Cl[C:42]([O:44][CH2:45][CH:46]([CH2:51][CH3:52])[CH2:47][CH2:48][CH2:49][CH3:50])=[O:43]>CN(C=O)C>[NH2:1][C:2](=[N:33][O:34][C:42]([O:44][CH2:45][CH:46]([CH2:51][CH3:52])[CH2:47][CH2:48][CH2:49][CH3:50])=[O:43])[C:3]1[CH:4]=[C:5]2[C:22](=[CH:23][CH:24]=1)[O:21][C:8]1([CH2:13][CH2:12][N:11]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:10][CH2:9]1)[CH2:7][CH:6]2[O:25][Si:26]([C:29]([CH3:32])([CH3:31])[CH3:30])([CH3:28])[CH3:27]

Participants

5

Reactant 3

HCID 1049PyridineHCID 627832-Ethylhexyl chloroformateHCID 76650868Tert-butyl 6-[amino(hydroxyimino)methyl]-4-{[tert-butyl(dimethyl)silyl]oxy}spiro[chroman-2,4'-piperidine]-1'-carboxylate

Product 1

HCID 76650869Tert-butyl 6-{amino[({[(2-ethylhexyl)oxy]carbonyl}oxy)-imino]methyl}-4-{[tert-butyl(dimethyl)silyl]oxy}spiro[chroman-2,4'-piperidine]-1'-carboxylate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of tert-butyl 6-[amino(hydroxyimino)methyl]-4-{[tert-butyl(dimethyl)silyl]oxy}-spiro[chroman-2,4′-piperidine]-1′-carboxylate in 80 mL of DMF were added 3.78 mL of pyridine and 8.4 mL of 2-Ethylhexyl chloroformate at 0° C., and the reaction mixture was stirred at 0° C. for 1.5 h. The reaction mixture was poured into ice-cold brine, and extracted with AcOEt twice. The combined organic layers were washed with H2O and brine, dried over Na2SO4, filtered, and concentrated in reduced pressure to give a crude product, which was used in the next step without further purification.

Workup

  1. additionThe reaction mixture was poured into ice-cold brine
  2. extractionextracted with AcOEt twice
  3. washThe combined organic layers were washed with H2O and brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in reduced pressure

Sources & evidence

ORD record
ord-0f241a17efab44d8b82d49b81c911579
Source dataset
uspto-grants-2012_03
Patent number
US08138197B2

Reaction notes

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