Stannous Chloride → HCID 69621532, compound

HRID 1830936Notes

Reaction equation

HRID 1830936 reaction equation
[CH2:1]([O:8][C:9]1[C:28]([O:29][CH3:30])=[CH:27][C:12]([C:13]([N:15]2[CH:19]=[C:18]([CH2:20][C:21]([O:23][CH3:24])=[O:22])[CH2:17][C@H:16]2[CH2:25][OH:26])=[O:14])=[C:11]([N+:31]([O-])=O)[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl[Sn]Cl.C(Cl)(Cl)Cl.CO>CO>[NH2:31][C:11]1[CH:10]=[C:9]([O:8][CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[C:28]([O:29][CH3:30])=[CH:27][C:12]=1[C:13]([N:15]1[CH:19]=[C:18]([CH2:20][C:21]([O:23][CH3:24])=[O:22])[CH2:17][C@H:16]1[CH2:25][OH:26])=[O:14]

Participants

5

Reactant 3

HCID 24479Stannous ChlorideHCID 21584188Chloroform methanolHCID 69621453HCID 69621453, compound

Product 1

HCID 69621532HCID 69621532, compoundYield 88.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of the nitro-alcohol 20 (0.35 g, 0.77 mmol) and SnCl2/2H2O (0.87 g, 3.86 mmol) in methanol (16 mL) was heated to reflux and monitored by TLC (90% CHCl3/MeOH). After 1 hour the MeOH was evaporated in vacuo and the resulting residue cooled (ice), and treated carefully with saturated NaHCO3 (65 mL). The mixture was diluted with EtOAc (65 mL), and after 16 hours stirring at room temperature the inorganic precipitate was removed by filtration through celite. The organic layer was separated, washed with brine (100 mL), dried (MgSO4), filtered and evaporated in vacuo to give the crude amine 21 as a pale orange glass (0.29 g, 88%) which was carried through to the next step without further purification or analysis due to the instability of the amine.

Workup

  1. temperatureto reflux
  2. customAfter 1 hour the MeOH was evaporated in vacuo
  3. temperaturethe resulting residue cooled (ice)
  4. additiontreated carefully with saturated NaHCO3 (65 mL)
  5. additionThe mixture was diluted with EtOAc (65 mL)
  6. customwas removed by filtration through celite
  7. customThe organic layer was separated
  8. washwashed with brine (100 mL)
  9. dry with materialdried (MgSO4)
  10. filtrationfiltered
  11. customevaporated in vacuo

Sources & evidence

ORD record
ord-24999163a99c44e6ae553ec4660e7c32
Source dataset
uspto-grants-2006_06
Patent number
US07067511B2

Reaction notes

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