Sulfuric acid magnesium salt (1:1) → HCID 66896211, compound

HRID 337573Notes

Reaction equation

HRID 337573 reaction equation
[CH3:1][C:2]([Si:5]([CH3:21])([CH3:20])[O:6][CH2:7][C:8]1[CH:9]=[C:10]2[C:15](=[C:16]([CH:18]=O)[CH:17]=1)[N:14]=[CH:13][CH:12]=[CH:11]2)([CH3:4])[CH3:3].S([O-])([O-])(=O)=O.[Mg+2].[CH:28]1([NH2:31])[CH2:30][CH2:29]1.[BH4-].[Na+]>CO.ClCCl>[CH3:1][C:2]([Si:5]([CH3:21])([CH3:20])[O:6][CH2:7][C:8]1[CH:9]=[C:10]2[C:15](=[C:16]([CH2:18][NH:31][CH:28]3[CH2:30][CH2:29]3)[CH:17]=1)[N:14]=[CH:13][CH:12]=[CH:11]2)([CH3:4])[CH3:3]

Participants

7

Reactant 4

HCID 24083Sulfuric acid magnesium salt (1:1)HCID 69828CyclopropylamineHCID 4311764Sodium borohydrideHCID 86651666HCID 86651666, compound

Product 1

HCID 66896211HCID 66896211, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

To a dichloromethane (0.12 M) solution of 6-({[(1,1-dimethylethyl)(dimethyl)silyl]oxy}methyl)-8-quinolinecarbaldehyde (1 eq.) from the previous step was added magnesium sulphate (1 eq.) and cyclopropyl amine (2 eq.). The resulting suspension was stirred at RT for 16 h. The insolubles were removed via filtration and rinsed with dichloromethane before the combined filtrate was concentrated in vacuo. The crude imine thus obtained was taken up in methanol (0.12 M) and then added sodium borohydride (1.5 eq.) portionwise. The reaction mixture was stirred at RT for 2 h. The volatiles were then removed in vacuo and the resulting residue was partitioned between ether and 1 N aq. NaOH. The aqueous layer was separated and back-extracted with ether. The combined organic extracts were washed further with water and brine, dried over Na2SO4, filtered and the filtrate concentrated in vacuo to afford the crude title compound as a yellow oil.

Workup

  1. customThe insolubles were removed via filtration
  2. washrinsed with dichloromethane before the combined filtrate
  3. concentrationwas concentrated in vacuo
  4. customThe crude imine thus obtained
  5. stirringThe reaction mixture was stirred at RT for 2 h
  6. customThe volatiles were then removed in vacuo
  7. customthe resulting residue was partitioned between ether and 1 N aq. NaOH
  8. customThe aqueous layer was separated
  9. extractionback-extracted with ether
  10. washThe combined organic extracts were washed further with water and brine
  11. dry with materialdried over Na2SO4
  12. filtrationfiltered
  13. concentrationthe filtrate concentrated in vacuo

Sources & evidence

ORD record
ord-465d30b6adc84dd4ad85d33a708562e5
Source dataset
uspto-grants-2014_11
Patent number
US08889714B2

Reaction notes

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