Dimethylamine → HCID 69660796, compound
Reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[C:5]2[C@H:11]1[CH2:15][CH2:14][C:13](=O)[CH2:12]1.[CH3:17][NH:18][CH3:19].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(O)C>[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[C:5]2[C@H:11]1[CH2:15][CH2:14][CH:13]([N:18]([CH3:19])[CH3:17])[CH2:12]1Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
A solution of (3S)-3-(5-fluoro-1H-indol-3-yl)-cyclopentanone (290 mg, 1.34 mMol), dimethylamine (2.0 M solution in THF, 6.7 mL, 13.4 mMol) in ethanol (10 mL) was stirred for 15 min. Sodium triacetoxyborohydride (1.1 g, 5.4 mMol) was added and the reaction stirred for 1 h. The reaction was extracted three times with ethyl acetate/aqueous sodium bicarbonate solution. The ethyl acetate extracts were dried over magnesium sulfate and concentrated in vacuo to give (3S)-3-(5-fluoro-1H-indol-3-yl)-cyclopentyl-dimethylamine (400 mg, 100%) as a cis/trans diastereomeric mixture. The diastereomeric mixture was separated by preparative chiral HPLC using a Chiralpak AD column (50×500 mm with 20 μm packing) and 10% ethanol/hexane (0.1% diethylamine added in hexane as modifier) as the eluent at a flow rate of 60 mL/min for 50 min. The UV detector was set at 280 nm, the injection loop volume was 10 mL, and the injection load was 35–165 mg in a ethanol/hexane (1:1) solution.
Workup
- extractionThe reaction was extracted three times with ethyl acetate/aqueous sodium bicarbonate solution
- dry with materialThe ethyl acetate extracts were dried over magnesium sulfate
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-73ecd619989941da82c40dcbe9193682
- Source dataset
- uspto-grants-2006_05
- Patent number
- US07049314B2
Reaction notes
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