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Cyclopentanone → 2-(2-Fluoro-pyridin-4-yl)-2-cyclo-pentylamino-1-(3-trifluoromethyl-phenyl)-ethanol

HRID 1884814
Notes
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Reaction equation

HRID 1884814 reaction equation
[NH2:1][CH:2]([C:15]1[CH:20]=[CH:19][N:18]=[C:17]([F:21])[CH:16]=1)[CH:3]([C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([C:11]([F:14])([F:13])[F:12])[CH:6]=1)[OH:4].[C:22]1(=O)[CH2:26][CH2:25][CH2:24][CH2:23]1.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+].C([O-])(O)=O.[Na+]>ClCCCl>[F:21][C:17]1[CH:16]=[C:15]([CH:2]([NH:1][CH:22]2[CH2:26][CH2:25][CH2:24][CH2:23]2)[CH:3]([C:5]2[CH:10]=[CH:9][CH:8]=[C:7]([C:11]([F:12])([F:13])[F:14])[CH:6]=2)[OH:4])[CH:20]=[CH:19][N:18]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 8452CyclopentanoneHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 155242512-Amino-2-(2-fluoropyridine-4-yl)-1-(3-trifluoromethylphenyl)ethanol

Product 1

HCID 155242522-(2-Fluoro-pyridin-4-yl)-2-cyclo-pentylamino-1-(3-trifluoromethyl-phenyl)-ethanolYield 92%

Reagents, catalysts & solvents

1
HCID 111,2-DichloroethaneSolvent

Procedure

The 2 -amino-2-(2-fluoro-pyridin-4-yl)- 1 -(3-trifluoromethyl-phenyl)-ethanol (5) (1.0 g, 3.3 mmol), cyclopentanone (0.42 g, 5.0 mmol), and Na(OAc)3BH (1.4 g, 6.7 mmol) in 1,2 dichloroethane (20 mL) were stirred under argon at RT for 15 hrs. The resulting mixture was treated with sat. aqueous NaHCO3 (50 mL), extracted with ethyl acetate (3×75 mL), dried (sodium sulfate), and concentrated. The resulting residue was purified by silica gel chromatography using 50% ethyl acetate in methylene chloride to give the title product (1.1 g, 92%). 1H NMR (300 MHz, CDCl3) d 8.05 (d, J=4.9 Hz, 1 H, Pyr), 7.51 (d, J=7.9 Hz, 1 H, Ar), 7.36 (t, J=7.8 Hz, 1 H, Ar), 7.32 (s, 1 H, Ar), 7.22 (d, J=7.9 Hz, 1 H, Ar), 6.81 (d, J=4.9 Hz, 1 H, Pyr), 6.64 (s, 1 H, Pyr), 5.00 (d, J=4.6 Hz, 1 H, PhCHOH), 4.01 (d, J=4.9 Hz, 1 H, CHCHNH), 2.99 (quin, J=3.0 Hz, 1 H, CH2CHCH2), 1.85-1.25 (m, 8 H, CH2).

Workup

  1. extractionextracted with ethyl acetate (3×75 mL)
  2. dry with materialdried (sodium sulfate)
  3. concentrationconcentrated
  4. customThe resulting residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-a17c0a4a29f64444ac14e60f4ba89667
Source dataset
uspto-grants-2004_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06767908B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes