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

HRID 2182688Notes

Reaction equation

HRID 2182688 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-67a45417868f4d12ac544a6b9f9c4ad0
Source dataset
uspto-grants-2005_05
Patent number
US06897224B2

Reaction notes

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