Sodium borohydride → 3-[1-(5-Fluoro-2-methoxyphenyl)cycloprop-1-yl]-1-(2-methylquinolin-5-ylamino)-2-(trifluoromethyl)propan-2-ol

HRID 2054967Notes

Reaction equation

HRID 2054967 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([O:31][CH3:32])=[C:6]([C:8]2([CH2:11][C:12]([C:27]([F:30])([F:29])[F:28])([OH:26])[CH:13]=[N:14][C:15]3[CH:24]=[CH:23][CH:22]=[C:21]4[C:16]=3[CH:17]=[CH:18][C:19]([CH3:25])=[N:20]4)[CH2:10][CH2:9]2)[CH:7]=1.[BH4-].[Na+]>CO.O1CCCC1>[F:1][C:2]1[CH:3]=[CH:4][C:5]([O:31][CH3:32])=[C:6]([C:8]2([CH2:11][C:12]([C:27]([F:28])([F:29])[F:30])([OH:26])[CH2:13][NH:14][C:15]3[CH:24]=[CH:23][CH:22]=[C:21]4[C:16]=3[CH:17]=[CH:18][C:19]([CH3:25])=[N:20]4)[CH2:9][CH2:10]2)[CH:7]=1

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 21948799HCID 21948799, compound

Product 1

HCID 219488813-[1-(5-Fluoro-2-methoxyphenyl)cycloprop-1-yl]-1-(2-methylquinolin-5-ylamino)-2-(trifluoromethyl)propan-2-ol

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

870 mg (1.95 mmol) of 3-[1-(5-fluoro-2-methoxyphenyl)cycloprop-1-yl]-1-(2-methylquinolin-5-ylimino)-2-(trifluoromethyl)propan-2-ol is reacted analogously to Example 37 with 96 mg (2.53 mmol) of sodium borohydride in 6.0 ml of methanol and 3.0 ml of tetrahydrofuran. After recrystallization from hexane and ethyl acetate, 790 mg (90% of theory) of the product is obtained.

Workup

  1. customAfter recrystallization from hexane and ethyl acetate, 790 mg (90% of theory) of the product
  2. customis obtained

Sources & evidence

ORD record
ord-a6a169e7f60a4530a16993bc4c6413c8
Source dataset
uspto-grants-2008_02
Patent number
US07329753B2

Reaction notes

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