Benzaldehyde → HCID 66704734, compound

(3S,4S)-3-Aminomethyl-1-benzyl-4-fluoropyrrolidine (186 mg) was dissolved in methanol (4 mL). To this solution, molecular sieves 4A (80.0 mg) and benzaldehyde (90.8 μL) were sequentially added and the mixture was stirred at room temperature for 1 hour. Subsequently, a borane-pyridine complex (90.2 μL) was added and the mixture was further stirred at room temperature for 3 hours. This was followed by addition of 6 mol/L hydrochloric acid (1.5 mL) and stirring for 1 hour. Subsequently, a 6 mol/L aqueous solution of sodium hydroxide was added to make the mixture basic and the mixture was extracted with diethyl ether (3×10 mL). The diethyl ether extracts were combined and the combined diethyl ether layer was dried over anhydrous sodium sulfate and was then concentrated under reduced pressure. The resulting residue was purified on a silica gel column (eluant=hexane:ethyl acetate=4:1) to give 179 mg of (3S,4S)-1-benzyl-3-benzylaminomethyl-4-fluoropyrrolidine as a pale brown oil.

1. additionSubsequently, a borane-pyridine complex (90.2 μL) was added
2. stirringthe mixture was further stirred at room temperature for 3 hours
3. stirringstirring for 1 hour
4. extractionthe mixture was extracted with diethyl ether (3×10 mL)
5. dry with materialthe combined diethyl ether layer was dried over anhydrous sodium sulfate
6. concentrationwas then concentrated under reduced pressure
7. customThe resulting residue was purified on a silica gel column (eluant=hexane:ethyl acetate=4:1)

ORD record

ord-3ac47a1d5c3a479bb50c4175775d85d8

Source dataset

uspto-grants-2006_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07153851B2