Sodium Hydroxide → HCID 178453656, compound

HRID 1485114Notes

Reaction equation

HRID 1485114 reaction equation
[N+](C1C=CC(C([O:10][C@H:11]2[CH2:14][C@H:13]([CH2:15][NH:16][C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:12]2)=O)=CC=1)([O-])=O.[OH-].[Na+]>O1CCCC1>[OH:10][C@H:11]1[CH2:14][C@H:13]([CH2:15][NH:16][C:17](=[O:18])[O:19][C:20]([CH3:22])([CH3:21])[CH3:23])[CH2:12]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 178453661HCID 178453661, compound

Product 1

HCID 178453656HCID 178453656, compoundYield 83.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution in tetrahydrofuran (100 mL) of the compound (3.88 g) obtained in step (1) above, an aqueous solution of 1 mol/L sodium hydroxide (19.9 mL) was added and the mixture was stirred at room temperature for 4 hours. Extraction was conducted with ethyl acetate and after drying the combined organic layers over anhydrous magnesium sulfate, the desiccant was removed by filtration. With the solvent being distilled off under reduced pressure, the crude product was adsorbed on diatomaceous earth. The crude product as adsorbed on the diatomaceous earth was purified by silica gel column chromatography (n-hexane:ethyl acetate=99:1-0:100, then chloroform:methanol=100:0-90:10) to give tert-butyl [(trans-3-hydroxycyclobutyl)methyl]carbamate as a colorless solid (1.87 g).

Workup

  1. extractionExtraction
  2. dry with materialafter drying the combined organic layers over anhydrous magnesium sulfate
  3. customthe desiccant was removed by filtration
  4. distillationWith the solvent being distilled off under reduced pressure
  5. customwas purified by silica gel column chromatography (n-hexane

Sources & evidence

ORD record
ord-de2d3bf5dc6a41e9958fcf3bce21675b
Source dataset
uspto-grants-2016_08
Patent number
US09422240B2

Reaction notes

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