Methanol → HCID 59994483, compound

HRID 2059931Notes

Reaction equation

HRID 2059931 reaction equation
[BH4-].[Li+].Cl[Si](C)(C)C.[CH3:8][C:9]1[C:14](/[CH:15]=[CH:16]/[N+:17]([O-])=O)=[CH:13][CH:12]=[CH:11][C:10]=1[O:20][CH3:21].CO>C1COCC1>[CH3:8][C:9]1[C:10]([O:20][CH3:21])=[CH:11][CH:12]=[CH:13][C:14]=1[CH2:15][CH2:16][NH2:17]

Participants

6

Reactant 4

HCID 887MethanolHCID 6397ChlorotrimethylsilaneHCID 4148881Lithium borohydrideHCID 59370485HCID 59370485, compound

Product 1

HCID 59994483HCID 59994483, compoundYield 48.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To lithium borohydride (2M in THF; 2.0 ml; 4.0 mmol) (cloudy) at room temperature was added dropwise over 0.5 min chlorotrimethylsilane (1.02 ml; 8.00 mmol). A precipitate was formed and after ca. 3 min, 2-methyl-1-(methyloxy)-3-[(E)-2-nitroethenyl]benzene (Preparation 9, 193 mg; 1.0 mmol) in THF (4 ml) was added dropwise via syringe over 5 min, making sure that the temperature remained at ca. 25° C. (using a water cold bath). The solution was stirred at room temperature overnight. The mixture was cooled with an ice bath, methanol was added slowly, and the solvent removed in vacuo. The residue was partitioned between 25% aqueous sodium hydroxide and dichloromethane. The aqueous phase was separated and extracted three times with dichloromethane and the combined organic layers evaporated. Purification of the residue by solid phase extraction (SCX column), eluting with methanol followed by 2N ammonia in methanol, followed by evaporation of the ammonia containing fraction gave the title compound (80 mg).

Workup

  1. customA precipitate was formed and after ca. 3 min
  2. customremained at ca. 25° C.
  3. temperatureThe mixture was cooled with an ice bath
  4. customthe solvent removed in vacuo
  5. customThe residue was partitioned between 25% aqueous sodium hydroxide and dichloromethane
  6. customThe aqueous phase was separated
  7. extractionextracted three times with dichloromethane
  8. customthe combined organic layers evaporated
  9. customPurification of the residue
  10. extractionby solid phase extraction (SCX column)
  11. washeluting with methanol
  12. customfollowed by evaporation of the ammonia containing fraction

Sources & evidence

ORD record
ord-20ffedb02285444da277fd95a7b1895a
Source dataset
uspto-grants-2012_10
Patent number
US08278324B2

Reaction notes

Loading…