Dimethyl Sulfoxide → HCID 57905221, compound

Temperature

-78 °C

To a solution of oxalyl chloride (3.44 mL, 39.3 mmol) in dichloromethane (200 mL) at −78° C. was added, dropwise, dry DMSO (4.36 mL, 61.4 mmol). After 10 min at −78° C., a solution of (3-((tert-butyldimethylsilyloxy)methyl)cyclopentyl)methanol (6.0 g, 24.56 mmol) in CH2Cl2 (180 mL) was slowly added and the mixture stirred at −78° C. After 1 h, triethylamine (17.11 mL, 122.8 mmol) was added and stirring continued at −78° C. for 10 min after which the mixture was allowed to warm to 23° C. The reaction mixture was diluted with HCl 1N (pH˜6) and the phases separated. The organic fraction was dried (MgSO4), filtered and concentrated in vacuo to give 5.81 g (97% yield) of the title compound as a light yellow oil. 1H NMR (400 MHz, CDCl3) δ ppm 9.62 (1 H, d, J=2.5 Hz), 3.54 (2 H, ddd, J=12.0, 10.0, 6.3 Hz), 2.73-2.82 (1 H, m), 2.14-2.24 (1 H, m), 1.89-2.00 (2 H, m), 1.74-1.85 (2 H, m), 1.57 (1 H, dt, J=13.1, 8.6 Hz), 1.33-1.44 (1 H, m), 0.91 (9 H, s), 0.06 (6 H, s).

1. waitAfter 1 h
2. stirringstirring
3. waitcontinued at −78° C. for 10 min
4. temperatureto warm to 23° C
5. customthe phases separated
6. dry with materialThe organic fraction was dried (MgSO4)
7. filtrationfiltered
8. concentrationconcentrated in vacuo

ORD record

ord-2f3bdb8612ec4491b955dfeb76382c77

Source dataset

uspto-grants-2012_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08129398B2