Dimethyl Sulfoxide → Tert-butyl 3-oxopyrrolidine-1-carboxylate

Temperature

0 °C

A solution of 2.3 mL (26 mmol) of oxalyl chloride in 80 mL of CH2Cl2 at −78° C. was treated with 3.8 mL (53 mmol) of DMSO in 5 mL of CH2Cl2. The resulting mixture was stirred cold for 5 min. A solution of 2.0 g (10.7 mmol) of (R/S)-1-tert-butoxycarbonyl-3-hydroxypyrrolidine (from Step A) in 10 mL of CH2Cl2 was added. The resulting mixture was stirred for 30 min, treated with 18.7 mL (107 mmol) of DIEA and warmed to 0° C. After stirring for 45 min, the reaction was quenched with H2O and poured into 100 mL of 1N HCl. After separating the layers, the organic layer was washed with 100 mL sat'd NaCl, dried over Na2SO4 and concentrated. The residue was purified on a 40M Biotage column using 4:1 v/v hexane/acetone as the eluant to afford 1.9 g (96%) of the title compound: RF: 0.49 (7:3 v/v hexane/acetone); 1H-NMR (500 MHz) δ 1.48 (s, 9H), 2.58 (t, J=7.9, 2H), 3.71-3.78 (m, 4H).

1. stirringThe resulting mixture was stirred for 30 min
2. stirringAfter stirring for 45 min
3. customthe reaction was quenched with H2O
4. additionpoured into 100 mL of 1N HCl
5. customAfter separating the layers
6. washthe organic layer was washed with 100 mL sat'd NaCl
7. dry with materialdried over Na2SO4
8. concentrationconcentrated
9. customThe residue was purified on a 40M Biotage column

ORD record

ord-78090b9692aa4dadbd84e1877532e717

Source dataset

uspto-grants-2009_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07479504B2