1,4-Dibromobutane → 1-Pyrrolidineethanol,beta-methyl-,(betaS)-(9CI)

A mixture of (S)-2-aminopropan-1-ol (566 mg, 7.54 mmol), 1,4-dibromobutane, and potassium carbonate (2.09 g, 15.1 mmol) in acetonitrile (70 mL) was heated at reflux overnight and allowed to cool to room temperature. The insoluble solid was filtered off, and the filtrate was concentrated under reduced pressure. The residue was diluted with DCM (75 mL) and washed (25 mL sat'd K2CO3). The aqueous phase was extracted with DCM (2×25 mL) and the combined organic extracts were dried over Na2SO4. The solvent was removed under reduced pressure and purified on a silica gel column to yield (S)-2-(pyrrolidin-1-yl)propan-1-ol (630 mg, 65%) as a clear oil. 1H NMR (CDCl3): δ 3.63 (m, 1H), 3.38 (m, 1H), 2.97 (br s, 1H), 2.69 (m, 1H), 2.60 (br s, 4H), 1.72 (br s, 4H), 1.06 (d, 3H).

1. temperaturewas heated
2. temperatureat reflux overnight
3. filtrationThe insoluble solid was filtered off
4. concentrationthe filtrate was concentrated under reduced pressure
5. additionThe residue was diluted with DCM (75 mL)
6. washwashed (25 mL sat'd K2CO3)
7. extractionThe aqueous phase was extracted with DCM (2×25 mL)
8. dry with materialthe combined organic extracts were dried over Na2SO4
9. customThe solvent was removed under reduced pressure
10. custompurified on a silica gel column

ORD record

ord-c1574465dff04a77990e41c007adbe03

Source dataset

uspto-grants-2014_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08703810B2