L-Alaninol → HCID 58743044, compound

(R)-2-Methylbutane-1,4-diyl dimethanesulfonate (37.5 g, 0.144 mol) was added to neat (S)-2-aminopropan-1-ol (54.8 g, 0.730 mol). The mixture was stirred in a room temperature water bath to minimize the exotherm. After 24 h, the reaction was diluted with DCM (150 mL), saturated aqueous K2CO3 solution (150 mL), and enough water (60 mL) to dissolve the resulting precipitate. The organic layer was separated and the aqueous layer was extracted with DCM (150 mL). The organic layers were combined, dried over (Na2SO4), filtered, concentrated, and purified by silica gel chromatography (10:7; ethyl acetate:hexanes→10:7:2:1; ethyl acetate:hexanes:methanol:triethylamine) to give (S)-2-((R)-3-methylpyrrolidin-1-yl)propan-1-ol (17.9 g) as a pale yellow oil. 1H NMR (400 MHz, DMSO-d6): δ 4.33 (t, 1H), 3.48 (m, 1H), 3.18 (m, 1H), 2.79 (dd, 1H), 2.58 (m, 1H), 2.48 (m, 1H), 2.26 (m, 1H), 2.08 (m, 1H), 2.01 (dd, 1H), 1.88 (m, 1H), 1.20 (m, 1H), 0.98 (d, 3H), 0.96 (d, 3H); LCMS: 144.3 (M+H)+.

1. dissolutionto dissolve the resulting precipitate
2. customThe organic layer was separated
3. extractionthe aqueous layer was extracted with DCM (150 mL)
4. dry with materialdried over (Na2SO4)
5. filtrationfiltered
6. concentrationconcentrated
7. custompurified by silica gel chromatography (10:7; ethyl acetate:hexanes→10:7:2:1; ethyl acetate:hexanes:methanol:triethylamine)

ORD record

ord-7983e327d18c44ac9984fe6c54d5623d

Source dataset

uspto-grants-2015_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09187460B2