Sodium borohydride → 4-(4-Chloro-2-methoxyphenyl)-1-(2-(hydroxymethyl)quinolin-5-ylamino)-4-methyl-2-(trifluoromethyl)pentan-2-ol

HRID 2215449Notes

Reaction equation

HRID 2215449 reaction equation
C[O:2][C:3]([C:5]1[CH:14]=[CH:13][C:12]2[C:7](=[CH:8][CH:9]=[CH:10][C:11]=2[N:15]=[CH:16][C:17]([OH:35])([C:31]([F:34])([F:33])[F:32])[CH2:18][C:19]([C:22]2[CH:27]=[CH:26][C:25]([Cl:28])=[CH:24][C:23]=2[O:29][CH3:30])([CH3:21])[CH3:20])[N:6]=1)=O.[BH4-].[Na+].CCCCCC.C(OCC)(=O)C>CO>[Cl:28][C:25]1[CH:26]=[CH:27][C:22]([C:19]([CH3:20])([CH3:21])[CH2:18][C:17]([C:31]([F:32])([F:34])[F:33])([OH:35])[CH2:16][NH:15][C:11]2[CH:10]=[CH:9][CH:8]=[C:7]3[C:12]=2[CH:13]=[CH:14][C:5]([CH2:3][OH:2])=[N:6]3)=[C:23]([O:29][CH3:30])[CH:24]=1

Participants

5

Reactant 3

HCID 4311764Sodium borohydrideHCID 21226206Ethyl acetate hexaneHCID 69204021HCID 69204021, compound

Product 1

HCID 219488084-(4-Chloro-2-methoxyphenyl)-1-(2-(hydroxymethyl)quinolin-5-ylamino)-4-methyl-2-(trifluoromethyl)pentan-2-ol

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Analogously to Example 40, 200 mg (0.39 mmol) of 5-[4-(4-chloro-2-methoxy-phenyl) -2-hydroxy-4-methyl-2-(trifluoromethyl)pentylidenamino]quinoline-2-carboxylic acid methyl ester is dissolved in 5.0 ml of methanol and mixed with 60 mg (1.56 mmol) of sodium borohydride. After chromatography on silica gel with hexane-ethyl acetate (0–100%), 70 mg (37% of theory) of the product is obtained.

Sources & evidence

ORD record
ord-2e7109d539a54660a7b513471539a62d
Source dataset
uspto-grants-2006_09
Patent number
US07109212B2

Reaction notes

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