Formaldehyde → 3-(4-Bromophenyl)-1-methylpyrrolidine

To a mixture of 3-(4-bromophenyl)pyrrolidine hydrochloride (200 mg, 0.76 mmol) in methanol (6 mL) was added triethylamine (77 mg, 0.76 mmol) and several drops of acetic acid. The reaction mixture was stirred at room temperature for 5 min and treated with aqueous formaldehyde (37%, 0.2 mL) and sodium triacetoxyborohydride (322 mg, 1.52 mmol). The reaction mixture was stirred for 18 h at room temperature. The methanol was evaporated in vacuo and the residue was partitioned between water and EtOAc. The phases were separated and the aqueous phase was back-extracted with EtOAc. The combined organic phases were washed with brine, dried over Na2SO4, and concentrated in vacuo to give 3-(4-bromophenyl)-1-methylpyrrolidine (0.247 g) as a solid, which was used in the next step without further purification. MS (ES+) 239.9 (M+H)+.

1. stirringThe reaction mixture was stirred for 18 h at room temperature
2. customThe methanol was evaporated in vacuo
3. customthe residue was partitioned between water and EtOAc
4. customThe phases were separated
5. extractionthe aqueous phase was back-extracted with EtOAc
6. washThe combined organic phases were washed with brine
7. dry with materialdried over Na2SO4
8. concentrationconcentrated in vacuo

ORD record

ord-66e7fa23bebf48ad85be84d53bb20039

Source dataset

uspto-grants-2016_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09394285B2