Methanol → 67824-38-8

To a solution of 5.99 g (0.052 mol) of (S)-(-)-1-methyl-2-hydroxymethylpyrrolidine in 30 ml of ethanol-free chloroform under nitrogen at 0° was added a solution of 4.75 ml (7.75 g, 0.065 mol) of thionyl chloride in 15 ml of ethanol-free chloroform over 10 min. The resultant clear, brown solution was stirred at room temperature for 30 min. and refluxed for 30 min. After cooling, the dark solution was evaporated to provide a tan-colored, solid residue. The residue was dissolved in absolute ethanol and excess ether was added resulting in the crystallization of a beige-colored solid. The solid was suction-filtered and dried under a nitrogen atmosphere affording 8.02 g (91%): mp 152°-154°; [α]D20 =-6°, c=2.35, methanol.

1. temperaturerefluxed for 30 min
2. temperatureAfter cooling
3. customthe dark solution was evaporated
4. customto provide a tan-colored, solid residue
5. customresulting in the crystallization of a beige-colored solid
6. filtrationThe solid was suction-filtered
7. customdried under a nitrogen atmosphere
8. customaffording 8.02 g (91%)

ORD record

ord-6c2296aa24ce4a09ab781ec8e365dd0b

Source dataset

uspto-grants-1982_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04321387