Hydrochloric Acid → HCID 131729986, compound

methyl 2-((2R,4R)-4-fluoro-1-(4-(2-methylbenzyl)phenyl)pyrrolidin-2-yl)acetate: A ˜3 M solution of HCl/MeOH/CH2Cl2/MeOAc was prepared by addition of acetyl chloride (0.64 mL) to a 1:1 solution of MeOH/CH2Cl2 (2.4 mL) at 0° C. The resulting solution of HCl was added to 37C (0.0051 g, 0.017 mmol). After stirring at rt for 2 h, the reaction was basified with sat. Na2CO3 (aq) and the desired product was extracted with CH2Cl2. The combined organic layers were washed with brine, dried (MgSO4), and concentrated. The crude product was purified by silica gel chromatography to provide 37D (yellow oil, 0.0021 g, 6.2 mmol, 37% yield). LC-MS Anal. Calc'd for C21H24FNO2 341.42. found [M+H] 342.0. 1H NMR (400 MHz, chloroform-d) δ ppm 7.14 (3 H, q, J=4.77 Hz), 7.07-7.11 (1 H, m), 7.01 (2 H, d, J=8.25 Hz), 6.56 (2 H, d, J=8.25 Hz), 5.30 (1 H, d, J=53.34 Hz), 4.29-4.38 (1 H, m), 3.89 (2 H, s), 3.67-3.69 (1 H, m), 3.63-3.75 (3 H, m), 3.50-3.61 (1 H, m), 2.99 (1 H, dd, J=15.40, 2.75 Hz), 2.54-2.68 (1 H, m), 2.25 (3 H, s), 2.17 (2 H, dd, J=15.40, 9.90 Hz).

1. extractionthe desired product was extracted with CH2Cl2
2. washThe combined organic layers were washed with brine
3. dry with materialdried (MgSO4)
4. concentrationconcentrated
5. customThe crude product was purified by silica gel chromatography

ORD record

ord-320cbf67af6c4e808ae764ae0f521522

Source dataset

uspto-grants-2012_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08288404B2