Sodium borohydride → 2-Amino-2-(4-fluorophenyl)-1-quinolin-8-ylethanol

HRID 1170386Notes

Reaction equation

HRID 1170386 reaction equation
[BH4-].[Na+].[F:3][C:4]1[CH:9]=[CH:8][C:7]([CH:10]([NH:23]C(=O)OC(C)(C)C)[C:11](=[O:22])[C:12]2[CH:13]=[CH:14][CH:15]=[C:16]3[C:21]=2[N:20]=[CH:19][CH:18]=[CH:17]3)=[CH:6][CH:5]=1>CO>[NH2:23][CH:10]([C:7]1[CH:6]=[CH:5][C:4]([F:3])=[CH:9][CH:8]=1)[CH:11]([C:12]1[CH:13]=[CH:14][CH:15]=[C:16]2[C:21]=1[N:20]=[CH:19][CH:18]=[CH:17]2)[OH:22]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 86621948Tert-butyl [1-(4-fluorophenyl)-2-oxo-2-quinolin-8-ylethyl]carbamate

Product 1

HCID 675239562-Amino-2-(4-fluorophenyl)-1-quinolin-8-ylethanolYield 40.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

0.48 g (13 mmol) of sodium borohydride was added to a solution of 4.9 g (13 mmol) of tert-butyl [1-(4-fluorophenyl)-2-oxo-2-quinolin-8-ylethyl]carbamate in 75 ml of methanol at 0-5° C. After 1 h, the reaction mixture was concentrated and diluted with ethyl acetate and water, and the organic phase was washed with saturated ammonium chloride and sodium bicarbonate solutions. The residue after drying of the organic phase and concentration was dissolved in 40 ml of methylene chloride, and 9 ml of trifluoroacetic acid were added. After 2 h, ice-water was added and the product was extracted into the aqueous phase. The aqueous phase was made alkaline, the product was extracted with methylene chloride, and 1.5 g of 2-amino-2-(4-fluorophenyl)-1-quinolin-8-ylethanol were obtained.

Workup

  1. concentrationthe reaction mixture was concentrated
  2. additiondiluted with ethyl acetate and water
  3. washthe organic phase was washed with saturated ammonium chloride and sodium bicarbonate solutions
  4. customThe residue after drying of the organic phase and concentration
  5. dissolutionwas dissolved in 40 ml of methylene chloride
  6. addition9 ml of trifluoroacetic acid were added
  7. waitAfter 2 h
  8. additionice-water was added
  9. extractionthe product was extracted into the aqueous phase
  10. extractionthe product was extracted with methylene chloride

Sources & evidence

ORD record
ord-84622a6de05844238116f5da25f8a12f
Source dataset
uspto-grants-2010_11
Patent number
US07825264B2

Reaction notes

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