Dichloromethane → HCID 86757201, compound

To a solution of (RS)-N-benzyl-3-pyrrolidinol (354 mg, 2.0 mmol) in CH2Cl2 (6 ml) was added diethylaminosulfur tetrafluoride (DAST) (0, 52 ml, 4.0 mmol) over 5 min. at 0-5° C. The mixture was stirred for a further 1.5 hrs. at r.t., then satd. NaHCO3 was added and the oragnic phase was further washed with NaHCO3 (10 ml). After drying the organic phase with Na2SO4 the residue was chromatographed over SiO2 (Merck 230-400 mesh) with nhexane/EtOAc (4:1) gradient to (1:1). The product was treated with HCl/ether to afford (RS)N-benzy-3-fluoropyrrolidine hydrochloride salt (190 mg, 1.06 mmol, 53% yield) as off-white crystals. This product (250 mg, 1.16 mmol) was then hydrogenated (1 atm. H2) in acetic acid (4 ml) at 100° C. with Pd/C (10%, 25 mg) for 24 hrs. The mixture was then evaporated and dissolved in MeOH, filtered though a celite pad and finally recrystallised from EtOAc/ether to afford the title compound (117 mg, 81% yield) as off-white crystals after drying under high vacuum. MS: m/e=89 (M+)

1. customat r.t.
2. washthe oragnic phase was further washed with NaHCO3 (10 ml)
3. dry with materialAfter drying the organic phase with Na2SO4 the residue
4. customwas chromatographed over SiO2 (Merck 230-400 mesh) with nhexane/EtOAc (4:1) gradient to (1:1)
5. additionThe product was treated with HCl/ether

ORD record

ord-614e295525c345099140ba10e3f02c74

Source dataset

uspto-grants-2001_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06265426B1