Nitrogen → HCID 90019723, compound

A solution of (±)-19 (250 mg, 1.81 mmol) in MeOH (2 ml) was cooled to −78° C. and a stream of ozone passed through until a blue colour persisted. N2 was then passed through the solution until the blue colour faded and excess ozone was removed. Me2S (1.12 g, 1.33 ml, 18.1 mmol) was added and stirring continued at −78° C. for 10 min before the cooling bath was removed and the reaction mixture stirred for 50 min. An N2 stream was then used to concentrate the reaction mixture. The residue was dissolved in THF (2 ml) and dibenzylammonium trifluoroacetate (113 mg, 0.36 mmol) added and the resulting solution stirred at room temperature for 22 h. An N2 stream was then used to concentrate the reaction mixture and the residue purified by column chromatography, eluting with 2:1 EtOAc:petrol, to afford the aldehyde (±)-20 (141 mg, 51%) as an orange oil. 1H NMR of this material showed it to be of sufficient purity for further reaction. A sample was re-columned to provide an analytical sample as a white solid.

1. customexcess ozone was removed
2. customwas removed
3. stirringthe reaction mixture stirred for 50 min
4. concentrationto concentrate the reaction mixture
5. dissolutionThe residue was dissolved in THF (2 ml)
6. stirringthe resulting solution stirred at room temperature for 22 h
7. concentrationto concentrate the reaction mixture
8. customthe residue purified by column chromatography
9. washeluting with 2:1 EtOAc

ORD record

ord-d8319f4b98654ed49c335b2004c1569f

Source dataset

uspto-grants-2016_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09242954B2