Water → HCID 21948877, compound

HRID 2215439Notes

Reaction equation

HRID 2215439 reaction equation
[C:1]([O:4][CH2:5][C:6]1[CH:15]=[CH:14][C:13]2[C:8](=[CH:9][CH:10]=[CH:11][C:12]=2[N:16]=[CH:17][C:18]([C:33]([F:36])([F:35])[F:34])([OH:32])[CH2:19][C:20]([C:23]2[CH:28]=[C:27]([F:29])[CH:26]=[CH:25][C:24]=2[O:30][CH3:31])([CH3:22])[CH3:21])[N:7]=1)(=[O:3])[CH3:2].[BH4-].[Na+].O>CO.O1CCCC1>[C:1]([O:4][CH2:5][C:6]1[CH:15]=[CH:14][C:13]2[C:8](=[CH:9][CH:10]=[CH:11][C:12]=2[NH:16][CH2:17][C:18]([C:33]([F:34])([F:35])[F:36])([OH:32])[CH2:19][C:20]([C:23]2[CH:28]=[C:27]([F:29])[CH:26]=[CH:25][C:24]=2[O:30][CH3:31])([CH3:22])[CH3:21])[N:7]=1)(=[O:3])[CH3:2]

Participants

6

Reactant 3

HCID 962WaterHCID 4311764Sodium borohydrideHCID 21948882HCID 21948882, compound

Product 1

HCID 21948877HCID 21948877, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution that consists of 170 mg (0.34 mmol) of 1-(2-(acetoxymethyl)quinolin-5-ylimino)-4-(5-fluoro-2-methoxyphenyl)-4-methyl-2-(trifluoromethyl)pentan-2-ol in 1.5 ml of methanol and 0.8 ml of tetrahydrofuran is mixed with 53 mg (1.38 mmol) of sodium borohydride. After 3 hours at room temperature, the reaction is halted by adding water. It is extracted with ethyl acetate, the combined organic phases are washed with saturated sodium chloride solution and dried on sodium sulfate. After removal of the solvent and chromatography on silica gel with hexane-ethyl acetate (0–100%), 94 mg (55% of theory) of the product is obtained.

Workup

  1. extractionIt is extracted with ethyl acetate
  2. washthe combined organic phases are washed with saturated sodium chloride solution
  3. customdried on sodium sulfate
  4. customAfter removal of the solvent and chromatography on silica gel with hexane-ethyl acetate (0–100%), 94 mg (55% of theory) of the product
  5. customis obtained

Sources & evidence

ORD record
ord-e1c2d6c73c5b4fcd9c563c0c5711f78e
Source dataset
uspto-grants-2006_09
Patent number
US07109212B2

Reaction notes

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