Sodium borohydride → HCID 23433598, compound

HRID 1604816Notes

Reaction equation

HRID 1604816 reaction equation
[C:1]([O:5][C:6]([N:8]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:11](=O)[C:10]([CH3:20])([CH3:19])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[BH4-].[Na+]>CO>[C:1]([O:5][C:6]([N:8]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH2:11][C:10]([CH3:20])([CH3:19])[CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 23433650HCID 23433650, compound

Product 1

HCID 23433598HCID 23433598, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 1-tert-butyloxycarbonyl-1,2,3,4-tetrahydro-3,3-dimethyl-4- quinolinone (128 mg, 0.47 mmol) in methanol (2 mL) at 0° C. was added portionwise sodium borohydride (18 mg, 0.47 mmol) and the reaction mixture was stirred at 0° C. for 3 h. The reaction mixture was then quenched with sat'd NH4Cl (2 mL), extracted with ethyl acetate (2×5 mL), dried (Na2SO4) and concentrated A solution of this crude material in ethyl acetate (3 mL) was hydrogenated under an atmosphere of hydrogen with 10% Pd/C (20 mg) and a trace of conc. H2SO4 at rt for 16 h. Filtration over Celite™ afforded 100 mg (84%) of 1-tert-butyloxycarbonyl-1,2,3,4-tetrahydro-3,3-dimethylquinoline. Data for

Workup

  1. customThe reaction mixture was then quenched with sat'd NH4Cl (2 mL)
  2. extractionextracted with ethyl acetate (2×5 mL)
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated A solution of this crude material in ethyl acetate (3 mL)
  5. waita trace of conc. H2SO4 at rt for 16 h
  6. filtrationFiltration over Celite™

Sources & evidence

ORD record
ord-4dddb303b4b14aa58219bc8e89d4ac1a
Source dataset
uspto-grants-1999_11
Patent number
US05994544

Reaction notes

Loading…