Hydrochloric Acid → HCID 58907336, compound

HRID 1295350Notes

Reaction equation

HRID 1295350 reaction equation
[N:1]([C:4]12[CH2:9][CH:8]1[CH2:7][N:6]([S:10]([C:13]1[CH:18]=[CH:17][C:16]([CH3:19])=[CH:15][CH:14]=1)(=[O:12])=[O:11])[CH:5]2[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=C=O.Cl>O1CCOCC1>[C:20]1([CH:5]2[N:6]([S:10]([C:13]3[CH:14]=[CH:15][C:16]([CH3:19])=[CH:17][CH:18]=3)(=[O:11])=[O:12])[CH2:7][CH:8]3[C:4]2([NH2:1])[CH2:9]3)[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 58907338HCID 58907338, compound

Product 1

HCID 58907336HCID 58907336, compoundYield 59%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a solution of racemic 1-isocyanato-2-phenyl-3-(toluene-4-sulfonyl)-3-aza-bicyclo[3.1.0]hexane Intermediate 5) in 1,4-dioxane (150 mL) was added 12% HCl aqueous (75 mL) dropwise and the reaction was allowed to stir for 16 hours at room temperature. The organic solvent was removed at reduced pressure and the flask containing the reaction residue was placed in a 0° C. bath. Methylene chloride and 2N NaOH were added until the pH of the aqueous layer was from about 9 to about 11. The layers were separated and the organic layer was washed with brine, dried over sodium sulfate, filtered, and the filtrate was concentrated to a crude weight of 3.9 g. This was adsorbed onto silica and flash chromatographed on silica with a gradient of 40% EtOAc/Hexanes to EtOAc as eluant. 2-Phenyl-3-(toluene-4-sulfonyl)-3-aza-bicyclo[3.1.0]hex-1-ylamine was obtained (2.0 g, 59% yield). The material was dissolved in hot chloroform and crystallized by adding a small amount of ether to the cooling solution.

Workup

  1. customThe organic solvent was removed at reduced pressure
  2. additionthe flask containing the reaction residue
  3. customwas placed in a 0° C.
  4. additionMethylene chloride and 2N NaOH were added until the pH of the aqueous layer
  5. customThe layers were separated
  6. washthe organic layer was washed with brine
  7. dry with materialdried over sodium sulfate
  8. filtrationfiltered
  9. concentrationthe filtrate was concentrated to a crude weight of 3.9 g
  10. customchromatographed on silica with a gradient of 40% EtOAc/Hexanes to EtOAc as eluant

Sources & evidence

ORD record
ord-34469b6378804d46a5c4930de5ce5383
Source dataset
uspto-grants-2007_07
Patent number
US07241798B2

Reaction notes

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