Hydrochloric Acid → (1S,3S)-N-[2,2-difluoro-2-(4-methylphenyl)ethyl]cyclopentane-1,3-diamine
Reaction equation
B.[NH2:2][C@H:3]1[CH2:7][CH2:6][C@H:5]([NH:8][C:9](=O)[C:10]([F:19])([F:18])[C:11]2[CH:16]=[CH:15][C:14]([CH3:17])=[CH:13][CH:12]=2)[CH2:4]1.Cl.C(=O)([O-])[O-].[Na+].[Na+]>C1COCC1>[F:18][C:10]([F:19])([C:11]1[CH:12]=[CH:13][C:14]([CH3:17])=[CH:15][CH:16]=1)[CH2:9][NH:8][C@H:5]1[CH2:6][CH2:7][C@H:3]([NH2:2])[CH2:4]1Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
1M borane in THF (20 mL, 20 mmol) was added slowly to a stirred solution of N-[(1S,3S)-3-aminocyclopentyl]-2,2-difluoro-2-(4-methylphenyl)acetamide (1.006 g, 3.749 mmol) in dry THF (20 mL) at 0° C. The reaction mixture was warmed to rt. and then was heated to 70° C. for 1 h. The reaction mixture was cooled, quenched with 6N HCl (2.5 mL, 15 mmol) and stirred at rt for 16 h. Aqueous sodium carbonate was added to pH=11, and the mixture was extracted with EtOAc, dried (MgSO4), filtered and concentrated. The resulting oil was purified by silica gel chromatography (eluting with 1.2% NH4OH/10.8% MeOH/CHCl3) to give the title compound as a pale yellow oil (627 mg): MS=255.4 (M+1).
Workup
- temperatureand then was heated to 70° C. for 1 h
- temperatureThe reaction mixture was cooled
- extractionthe mixture was extracted with EtOAc
- dry with materialdried (MgSO4)
- filtrationfiltered
- concentrationconcentrated
- customThe resulting oil was purified by silica gel chromatography (eluting with 1.2% NH4OH/10.8% MeOH/CHCl3)
Sources & evidence
- ORD record
- ord-3ac239e24c7047e699a5a40fd086706f
- Source dataset
- uspto-grants-2008_11
- Patent number
- US07452893B2
Reaction notes
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