Hydrochloric Acid → HCID 68703275, compound

HRID 2102961Notes

Reaction equation

HRID 2102961 reaction equation
[CH:1]([C:3]1[CH:4]=[N:5][C:6]2[C:11]([CH:12]=1)=[CH:10][CH:9]=[C:8]([NH:13][C:14](=[O:23])[O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[CH:7]=2)=[O:2].C1COCC1.[BH4-].[Na+].Cl>O.CO>[OH:2][CH2:1][C:3]1[CH:4]=[N:5][C:6]2[C:11]([CH:12]=1)=[CH:10][CH:9]=[C:8]([NH:13][C:14](=[O:23])[O:15][CH2:16][C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1)[CH:7]=2

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 4311764Sodium borohydrideHCID 59138727HCID 59138727, compound

Product 1

HCID 68703275HCID 68703275, compoundYield 64.9%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a stirred mixture of benzyl 3-formylquinolin-7-ylcarbamate (2.0 g, 0.0065 mol), THF (50 mL), MeOH (50 mL), and water (50 mL) was added sodium tetrahydroborate (0.25 g, 0.0065 mol). The mixture was stirred at rt until LC-MS indicated no SM. The mixture was acidified with 1N HCl and concentrated under vacuum, and then treated with aq. NaHCO3 solution and EtOAc. The organic layer was separated and washed with brine, dried (Na2SO4), and evaporated. The residue was purified by column chromatography on silica gel using MeOH-EtOAc (0-10%) as eluent to give the product (1.3 g, 64%) as a light yellow solid. LC-MS: 1.83 min, 309.2 (M+1).

Workup

  1. concentrationconcentrated under vacuum
  2. additiontreated with aq. NaHCO3 solution and EtOAc
  3. customThe organic layer was separated
  4. washwashed with brine
  5. dry with materialdried (Na2SO4)
  6. customevaporated
  7. customThe residue was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-36a544c5d7d64b12adf085326165f0a9
Source dataset
uspto-grants-2009_08
Patent number
US07576099B2

Reaction notes

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