Dimethyl Sulfoxide → HCID 118415290, compound

Temperature

-78 °C

To a solution of oxalyl chloride (8.7 g, 68.5 mmol, 2.0 eq) in anhydrous dichloromethane (200 mL) was added drop-wise a solution of DMSO (10.7 g, 137 mmol, 4.0 eq) in anhydrous dichloromethane (20 mL) at −78° C. under nitrogen. After 1 hour, a solution of (S)-2-(benzyl(methyl)amino)-2-cyclopentylethanol (4) (8.0 g, 34.3 mmol, 1.0 eq) in anhydrous dichloromethane (30 mL) was added drop-wise at −78° C. The reaction mixture was allowed to stir for another 1 hour at −78° C. Then triethylamine (27.8 g, 274 mmol, 8.0 eq) was added drop-wise at −78° C. After the addition the reaction mixture was warmed to 0° C. under stirring. After 30 min at 0° C., water (250 mL) was added into the reaction solution and the organic phase was washed with brine, dried over sodium sulphate and concentrated in vacuo to give the product 5 as an oil (quant); LC-MS: m/z 232 [M+H+]+.

1. additionAfter the addition the reaction mixture
2. temperaturewas warmed to 0° C.
3. stirringunder stirring
4. waitAfter 30 min at 0° C.
5. washthe organic phase was washed with brine
6. dry with materialdried over sodium sulphate
7. concentrationconcentrated in vacuo

ORD record

ord-e18fd9d7755a4089b0a5c2046764eaee

Source dataset

uspto-grants-2016_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09260478B2