Sulfuric acid magnesium salt (1:1) → HCID 57280542, compound

HRID 264610Notes

Reaction equation

HRID 264610 reaction equation
[CH2:1]([C@@H:8]1[CH2:13][C@@H:12]([NH2:14])[CH2:11][CH2:10][N:9]1[C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N:22]1[C:31]2[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=2)[C:25]([CH:32]=O)=[CH:24][CH:23]=1.S([O-])([O-])(=O)=O.[Mg+2].[BH4-].[Na+]>C1(C)C=CC=CC=1>[CH2:1]([C@@H:8]1[CH2:13][C@@H:12]([NH:14][CH2:32][C:25]2[C:26]3[C:31](=[CH:30][CH:29]=[CH:28][CH:27]=3)[N:22]=[CH:23][CH:24]=2)[CH2:11][CH2:10][N:9]1[C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 24083Sulfuric acid magnesium salt (1:1)HCID 780724-QuinolinecarboxaldehydeHCID 4311764Sodium borohydrideHCID 21970305HCID 21970305, compound

Product 1

HCID 57280542HCID 57280542, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 5 g (17.2 mmol) of (2R*,4S*)-2-benzyl-1-t-butyloxycarbonyl-4-piperidinamine and 2.7 g (17.2 mmol) of quinoline-4-carboxaldehyde in 50 ml of toluene is stirred at room temperature and, after 2 hours, 2.8 g (23.3 mmol) of anhydrous magnesium sulfate are added. After a further 16 hours, the mixture is filtered and the filtrate is concentrated. The brown oil is dissolved in 50 ml of methanol, and 0.69 g (18.3 mmol) of sodium borohydride is added in 4 portions. After stirring at room temperature for 3 hours, the reaction mixture is concentrated, taken in ethyl acetate and washed with water and brine. The organic phases are dried over magnesium sulfate and evaporated to dryness. The brown oil is chromatographed on silica gel with methylene chloride/methanol/conc. ammonia 850:50:1). The title compound is obtained as yellow oil. TLC: methylene chloride/methanol/conc. ammonia (700:50:1) Rf =0.38, FD-MS: M+ =431.

Workup

  1. waitAfter a further 16 hours
  2. filtrationthe mixture is filtered
  3. concentrationthe filtrate is concentrated
  4. dissolutionThe brown oil is dissolved in 50 ml of methanol
  5. stirringAfter stirring at room temperature for 3 hours
  6. concentrationthe reaction mixture is concentrated
  7. washwashed with water and brine
  8. dry with materialThe organic phases are dried over magnesium sulfate
  9. customevaporated to dryness
  10. customThe brown oil is chromatographed on silica gel with methylene chloride/methanol/conc

Sources & evidence

ORD record
ord-6dce2338fd42412aa42a756193589955
Source dataset
uspto-grants-1997_07
Patent number
US05646144

Reaction notes

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