Triethylamine → HCID 19001608, compound

A solution of dimethylsulphoxide (1.7 ml) in dichloromethane (10 ml) was added dropwise over 5 min to a stirred solution of oxalyl chloride (1.0 ml) in dichloromethane (20 ml) at - 72° under nitrogen. The resultant solution was stirred at - 72° for 5 min then a suspension of 3-(2-hydroxyethyl)-1-methyl-2-pyrrolidinone (1.30 g) in dichloromethane (10 ml) and dimethylsulphoxide (1 ml; added to improve dissolution of the alcohol) was added dropwise over 8 min. The resultant cloudy solution was stirred at - 72° for 15 min then treated with triethylamine (7.0 ml). The resultant suspension was warmed to room temperature and stirred at room temperature for 1 h. The suspension was filtered. The residue was washed with ethyl acetate. The combined filtrate and washings were evaporated to give a semi-solid which was chromatographed using a mixture of ethyl acetate and methanol (5:1) as the eluent, to give the title compound (743 mg).

1. additionadded
2. additionwas added dropwise over 8 min
3. stirringstirred at room temperature for 1 h
4. filtrationThe suspension was filtered
5. washThe residue was washed with ethyl acetate
6. customThe combined filtrate and washings were evaporated
7. customto give a semi-solid which
8. customwas chromatographed
9. additiona mixture of ethyl acetate and methanol (5:1) as the eluent

ORD record

ord-b8b274f660d14308b1887bf1b383e525

Source dataset

uspto-grants-1995_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05475020