Water → HCID 21948903, compound

HRID 2215419Notes

Reaction equation

HRID 2215419 reaction equation
[CH2:1]([C:3]1[CH:12]=[CH:11][C:10]2[C:5](=[CH:6][CH:7]=[CH:8][C:9]=2[N:13]=[CH:14][C:15]([C:30]([F:33])([F:32])[F:31])([OH:29])[CH2:16][C:17]([C:20]2[CH:25]=[C:24]([F:26])[CH:23]=[CH:22][C:21]=2[O:27][CH3:28])([CH3:19])[CH3:18])[N:4]=1)[CH3:2].[BH4-].[Na+].O>CO>[CH2:1]([C:3]1[CH:12]=[CH:11][C:10]2[C:5](=[CH:6][CH:7]=[CH:8][C:9]=2[NH:13][CH2:14][C:15]([C:30]([F:31])([F:32])[F:33])([OH:29])[CH2:16][C:17]([C:20]2[CH:25]=[C:24]([F:26])[CH:23]=[CH:22][C:21]=2[O:27][CH3:28])([CH3:19])[CH3:18])[N:4]=1)[CH3:2]

Participants

5

Reactant 3

HCID 962WaterHCID 4311764Sodium borohydrideHCID 21948825HCID 21948825, compound

Product 1

HCID 21948903HCID 21948903, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

600 mg (1.3 mmol) of 1-(2-ethylquinolin-5-ylimino)-4-(5-fluoro-2-methoxyphenyl)-4-methyl-2-(trifluoromethyl)pentan-2-ol in 5.0 ml of methanol is mixed at 0° C. with 197 mg (5.2 mmol) of sodium borohydride. After 2 hours at room temperature, water is added, and methanol is removed in a vacuum. The aqueous phase is extracted with dichloromethane, the combined organic phases are dried on sodium sulfate, and the solvent is removed in a vacuum. After purification on silica gel with hexane-ethyl acetate (0–100%), 400 mg (66% of theory) of the product is obtained.

Workup

  1. custommethanol is removed in a vacuum
  2. extractionThe aqueous phase is extracted with dichloromethane
  3. customthe combined organic phases are dried on sodium sulfate
  4. customthe solvent is removed in a vacuum
  5. customAfter purification on silica gel with hexane-ethyl acetate (0–100%), 400 mg (66% of theory) of the product
  6. customis obtained

Sources & evidence

ORD record
ord-038cc1f624964c22a634b3f7925c9d8f
Source dataset
uspto-grants-2006_09
Patent number
US07109212B2

Reaction notes

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