Sodium Carbonate → HCID 86682894, compound

Temperature

100 °C

A mixture of (S)-2-aminopropan-1-ol (12.5 g, 0.166 mol), 1,4-dibromopentane (42 g, 0.18 mol) and Na2CO3 (53 g, 0.51 mol) in EtOH (800 mL) was heated at 100° C. for 24 h. The mixture was filtered, and the filter cake was washed with EtOH (50 mL). The combined filtrate was concentrated under reduced pressure, and the crude product was purified on a silica gel column (NH4OH/MeOH/DCM=1/6/300) to give (S)-2-((S)-2-methylpyrrolidin-1-yl)propan-1-ol (2.1 g) as a colorless oil and a crude mixture containing (S)-2-(R)-2-methylpyrrolidin-1-yl)propan-1-ol. 1H NMR (DMSO-d6): δ 4.22 (br s, 1H), 3.36 (dd, 1H), 3.22 (dd, 1H), 2.82 (m, 1H), 2.65 (m, 2H), 2.42 (q, 1H), 1.78 (m, 1H), 1.60 (m, 2H), 1.25 (m, 1H), 0.95 (d, 3H), 0.84 (d, 3H); LCMS: 144 (M+H)+.

1. filtrationThe mixture was filtered
2. washthe filter cake was washed with EtOH (50 mL)
3. concentrationThe combined filtrate was concentrated under reduced pressure
4. customthe crude product was purified on a silica gel column (NH4OH/MeOH/DCM=1/6/300)

ORD record

ord-e0b3b6e434954e1fbeb40b683751a65b

Source dataset

uspto-grants-2014_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08703810B2