4-Methylmorpholine → HCID 86605650, compound

HRID 1986476Notes

Reaction equation

HRID 1986476 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][C:10]1[C:11]([CH2:30][CH:31]([CH3:33])[CH3:32])=[N:12][C:13]2[C:18]([C:19]=1[C:20]1[CH:25]=[CH:24][C:23]([CH3:26])=[CH:22][CH:21]=1)=[CH:17][C:16]([C:27](O)=[O:28])=[CH:15][CH:14]=2)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(Cl)(=O)OCC.CN1CCOCC1.[BH4-].[Na+]>O1CCCC1.O.CO>[OH:28][CH2:27][C:16]1[CH:17]=[C:18]2[C:13](=[CH:14][CH:15]=1)[N:12]=[C:11]([CH2:30][CH:31]([CH3:33])[CH3:32])[C:10]([CH2:9][NH:8][C:6](=[O:7])[O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[C:19]2[C:20]1[CH:25]=[CH:24][C:23]([CH3:26])=[CH:22][CH:21]=1

Participants

8

Reactant 4

HCID 79724-MethylmorpholineHCID 10928Ethyl chloroformateHCID 4311764Sodium borohydrideHCID 68830056HCID 68830056, compound

Product 1

HCID 86605650HCID 86605650, compoundYield 55.7%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 3-{[(tert-butoxycarbonyl)amino]methyl}-2-isobutyl-4-(4-methylphenyl)quinoline-6-carboxylic acid (4.48 g, 10 mmol) in tetrahydrofuran (50 ml) were added dropwise ethyl chlorocarbonate (1.6 ml, 15-mmol) and N-methylmorpholine (1.6 ml, 15 mmol) at 0° C., and after the completion of the dropwise addition, the mixture was stirred at 0° C. for 10 min. Sodium tetrahydroborate (1.32 g, 35 mmol) and methanol (10 ml) were added to the reaction mixture and the mixture was stirred at room temperature for 6 hrs. The reaction mixture was poured into water and extracted with ethyl acetate. The extract was washed with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure and the residue was crystallized from tetrahydrofuran-diisopropyl ether to give tert-butyl [6-(hydroxymethyl)-2-isobutyl-4-(4-methylphenyl)quinolin-3-yl]methylcarbamate (2.42 g, yield 55%) as white crystals.

Workup

  1. additionafter the completion of the dropwise addition
  2. stirringthe mixture was stirred at room temperature for 6 hrs
  3. extractionextracted with ethyl acetate
  4. washThe extract was washed with saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customThe solvent was evaporated under reduced pressure
  7. customthe residue was crystallized from tetrahydrofuran-diisopropyl ether

Sources & evidence

ORD record
ord-cac589df2c914b7bb3ab1c97000117c5
Source dataset
uspto-grants-2009_06
Patent number
US07547710B2

Reaction notes

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