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3-Fluoro-4-(trifluoromethyl)benzaldehyde → [(3RS,4SR)-1-Benzyl-4-(4-chloro-3-fluoro-phenyl)-pyrrolidin-3-yl]-(3-fluoro-4-trifluoromethyl-benzyl)-methyl-amine

HRID 2066984
Notes
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Reaction equation

HRID 2066984 reaction equation
[CH2:1]([N:8]1[CH2:12][CH:11]([C:13]2[CH:18]=[CH:17][C:16]([Cl:19])=[C:15]([F:20])[CH:14]=2)[CH:10]([NH:21][CH3:22])[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[F:23][C:24]1[CH:25]=[C:26]([CH:29]=[CH:30][C:31]=1[C:32]([F:35])([F:34])[F:33])[CH:27]=O.[BH3-]C#N.[Na+]>CO.CC(O)=O>[CH2:1]([N:8]1[CH2:12][CH:11]([C:13]2[CH:18]=[CH:17][C:16]([Cl:19])=[C:15]([F:20])[CH:14]=2)[CH:10]([N:21]([CH2:27][C:26]2[CH:29]=[CH:30][C:31]([C:32]([F:33])([F:34])[F:35])=[C:24]([F:23])[CH:25]=2)[CH3:22])[CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 27375373-Fluoro-4-(trifluoromethyl)benzaldehydeHCID 5003444Sodium cyanoborohydrideHCID 67398566[(3RS,4SR)-1-Benzyl-4-(4-chloro-3-fluoro-phenyl)-pyrrolidin-3-yl]-methyl-amine

Product 1

HCID 86641316[(3RS,4SR)-1-Benzyl-4-(4-chloro-3-fluoro-phenyl)-pyrrolidin-3-yl]-(3-fluoro-4-trifluoromethyl-benzyl)-methyl-amineYield 28%

Reagents, catalysts & solvents 2

HCID 176
Acetic Acid
Solvent
HCID 887MethanolSolvent2×

Procedure

To a stirred solution of [(3RS,4SR)-1-benzyl-4-(4-chloro-3-fluoro-phenyl)-pyrrolidin-3-yl]-methyl-amine (340 mg, 1.06 mmol) in MeOH (6 ml) was added 3-fluoro-4-trifluoromethyl-benzaldehyde (230 mg, 1.20 mmol). Then a solution of NaBH3CN (85 mg, 1.3 mol) in MeOH (1.5 ml) and AcOH (0.01 ml) were added. The reaction mixture was stirred overnight at RT, concentrated under vacuo, diluted with EtOAc, washed with H2O. The organic phases were dried over Na2SO4 and the product purified by flash chromatography (SiO2, EtOAc/Heptane 1:4) to afford 145 mg (28%) of the title compound as a colorless oil.

Workup

  1. concentrationconcentrated under vacuo
  2. additiondiluted with EtOAc
  3. washwashed with H2O
  4. dry with materialThe organic phases were dried over Na2SO4
  5. customthe product purified by flash chromatography (SiO2, EtOAc/Heptane 1:4)

Sources & evidence

ORD record
ord-cf1afda8572e4267b1f11ab137f5c95c
Source dataset
uspto-grants-2012_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08293770B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes