Homoallyl bromide → (2S,4S)-1-But-3-enyl-4-fluoro-pyrrolidine-2-carboxylic acid methyl ester

Temperature

70 °C

In a 25 mL round-bottomed flask, (2S,4S)-methyl 4-fluoropyrrolidine-2-carboxylate hydrochloride (160 mg, 871 μmol, Eq: 1.00) was combined with acetonitrile (3 mL) to give a white suspension. Hunig's base (282 mg, 380 μL, 2.18 mmol, Eq: 2.50) and 4-bromobut-1-ene (144 mg, 108 μL, 1.05 mmol, Eq: 1.20) were added sequentially. The reaction mixture was stirred at 70° C. for 2 days. The crude reaction mixture was concentrated in vacuo. The reaction mixture was poured into an aqueous 5% Na2CO3 solution and extracted with DCM (2×). The organic layers were combined, washed with brine (1×), the organic layers were dried over Na2SO4 and concentrated in vacuo to yield a yellow liquid (160 mg; 91%). m/z=202.2 [M+H]+.

1. customto give a white suspension
2. customThe crude reaction mixture
3. concentrationwas concentrated in vacuo
4. additionThe reaction mixture was poured into an aqueous 5% Na2CO3 solution
5. extractionextracted with DCM (2×)
6. washwashed with brine (1×)
7. dry with materialthe organic layers were dried over Na2SO4
8. concentrationconcentrated in vacuo
9. customto yield a yellow liquid (160 mg; 91%)

ORD record

ord-ec5196668c0949e3aadc2735580afd83

Source dataset

uspto-grants-2016_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09290467B2