Bicarbonate Ion → HCID 87457533, compound

To a solution of (5-(cyclopropylmethoxy)pyridin-2-yl)methanol (4.5 g, 25 mmol) in dichloromethane (50 ml), was added a 15% potassium bromide aqueous solution (20 mL) followed by a saturated bicarbonate solution (20 ml). The biphasic mixture was cooled in an ice bath and TEMPO (200 mg, 1.3 mmol) was added. After stirring for 10 min, 5% sodium hypochlorite (30 ml) was dropwised. The reaction mixture was stirred for 10 min. The solution was poured into a separatory funnel and the organic layer was dried over magnesium sulfate and concentrated in vacuo. The residue was dissolved in dichloromethane (50 mL). Copper(II) sulfate (10.1 g, 63 mmol) followed by (R)-(+)-2-methyl-2-propanesulfinamide (3.1 g, 25 mmol) were added to the mixture respectively and the mixture was stirred for 18 hours at room temperature. The reaction mixture was filtrated off and the filtrate was concentrated in vacuo. The residue was purified by column chromatography on silica gel eluting with hexane/ethyl acetate (1:1 (v/v)) to give 6.2 g (87% yield) of the title compound as a flaky solid:

1. temperatureThe biphasic mixture was cooled in an ice bath
2. stirringThe reaction mixture was stirred for 10 min
3. additionThe solution was poured into a separatory funnel
4. dry with materialthe organic layer was dried over magnesium sulfate
5. concentrationconcentrated in vacuo
6. dissolutionThe residue was dissolved in dichloromethane (50 mL)
7. additionwere added to the mixture respectively
8. stirringthe mixture was stirred for 18 hours at room temperature
9. filtrationThe reaction mixture was filtrated off
10. concentrationthe filtrate was concentrated in vacuo
11. customThe residue was purified by column chromatography on silica gel eluting with hexane/ethyl acetate (1:1 (v/v))

ORD record

ord-89a2faa1a602480eb90831035c8f4a22

Source dataset

uspto-grants-2015_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09101616B2