Triethylamine → HCID 178455648, compound

To a round bottomed flask equipped with magnetic stirrer charged with cis-4-(2,4-bis{[tert-butyl(dimethyl)silyl]oxy}phenyl)cyclohexylamine (150 mg, 0.34 mmol) and 1,2-dichloroethane (8 ml), was added triethylamine (96 μl, 0.70 mmol) and n-butylsulfonyl chloride (55 μl, 0.40 mmol) at room temperature. 4-Dimethylaminopyridine (3 crystals) was added and the mixture stirred for 17 hr. Aqueous sodium hydroxide solution (15 ml, 0.40M) was added and the mixture stirred for 10 min. The layers were partitioned and the aqueous layer was extracted with dichloromethane (15 ml). The combined organic layers were washed with brine (15 ml), dried over magnesium sulfate, filtered and concentrated in vacuo. The resulting solid was then dissolved in tetrahydrofuran (10 ml) and acetic acid (0.15 ml), then tetra-n-butylammonium fluoride hydrate (360 mg, 1.4 mmol) was added. The mixture was stirred at room temperature for 1 hr, then ethyl acetate (10 ml) and water (15 ml) were added. The layers were partitioned and the aqueous layer was extracted with ethyl acetate (10 ml). The combined organic layers were washed with brine (10 ml), dried over magnesium sulfate, filtered and concentrated in vacuo to leave an oil. Purification via flash column chromatography (SiO2, ethyl acetate/petroleum ether, 1:10 then 1:1, v/v) furnished the title compound (40 mg, 35%) as a white solid. m/z (ES−) 326 (M−H+); δH(CD3OD) 0.95 (3H, t), 1.45-1.55 (2H, m), 1.55-1.95 (10H, m), 2.80-2.90 (1H, m), 3.00-3.20 (2H, m), 3.65 (1H, m), 6.22-6.26 (2H, m), 6.96 (1H, d).

1. customTo a round bottomed flask equipped with magnetic stirrer
2. stirringthe mixture stirred for 10 min
3. customThe layers were partitioned
4. extractionthe aqueous layer was extracted with dichloromethane (15 ml)
5. washThe combined organic layers were washed with brine (15 ml)
6. dry with materialdried over magnesium sulfate
7. filtrationfiltered
8. concentrationconcentrated in vacuo
9. dissolutionThe resulting solid was then dissolved in tetrahydrofuran (10 ml)
10. stirringThe mixture was stirred at room temperature for 1 hr
11. customThe layers were partitioned
12. extractionthe aqueous layer was extracted with ethyl acetate (10 ml)
13. washThe combined organic layers were washed with brine (10 ml)
14. dry with materialdried over magnesium sulfate
15. filtrationfiltered
16. concentrationconcentrated in vacuo
17. customto leave an oil
18. customPurification via flash column chromatography (SiO2, ethyl acetate/petroleum ether, 1:10

ORD record

ord-5844baae075f404f97bc9509cb24b927

Source dataset

uspto-grants-2005_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06933319B2