Dimethylformamide → 5-Bromomethyl-2chloro-N-(tricyclo[3.3.1.13,7]dec-1-ylmethyl)-benzamide

To a stirred solution of 5-bromomethyl-2-chloro-benzoic acid (Example 71 a, 12.4 g) in dichloromethane (250 ml) and dimethylformamide (0.12 ml) at 0° C. was added oxalyl chloride (8.7 ml). The cooling bath was removed and the solution allowed to warm to room temperature. Once gas evolution had ceased the solution was concentrated in vacuo. The residue was redissolved in dichloromethane (300 ml), cooled to 0° C. and treated with diisopropylethylamine (12.4 ml) and adamantylmethylamine (7.54 ml). After 15 min at 0° C. the solution was poured into diethyl ether (1 L) and washed with 1N aqueous hydrochloric acid followed by brine. The organics were dried over magnesium sulphate and concentrated in vacuo to give the title compound as a white powder (19 g)

1. customThe cooling bath was removed
2. concentrationwas concentrated in vacuo
3. dissolutionThe residue was redissolved in dichloromethane (300 ml)
4. temperaturecooled to 0° C.
5. additiontreated with diisopropylethylamine (12.4 ml) and adamantylmethylamine (7.54 ml)
6. additionAfter 15 min at 0° C. the solution was poured into diethyl ether (1 L)
7. washwashed with 1N aqueous hydrochloric acid
8. dry with materialThe organics were dried over magnesium sulphate
9. concentrationconcentrated in vacuo

ORD record

ord-96152ccc45ec4414b347763e1c2e8070

Source dataset

uspto-grants-2006_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07132457B2