Triethylamine → HCID 178473658, compound

Triethylamine (0.5 ml), ethylchloroformate (0.5 ml) and dimethylaminopyridine (cat.) were added to a stirred solution of trans-4-(2,4-bis{[tert-butyl(dimethyl)silyl]oxy}phenyl)cyclohexanol (250 mg) in anhydrous dichloromethane (5 ml). After 72 hr at room temperature, the reaction mixture was partitioned between-ethyl-acetate (50 ml) and water (50 ml). The aqueous layer was extracted with ethyl acetate (2×50 ml). The combined organic extracts were washed with brine (50 ml), dried over magnesium sulfate and evaporated in vacuo. The residue was dissolved in methanol (5 ml) and was stirred with fluoride resin (500 mg) for 16 h at room temperature. The resin was filtered through a pad of celite, which was washed well with methanol. The combined filtrates were concentrated in vacuo. The residue was purified using flash column chromatography (SiO2, ethyl acetate/petrol, 1:2 v/v), and then preparative HPLC to give the title compound (4 mg, 3%) as a cream solid. δH (CD3OD) 1.20-1.30 (3H, m), 1.40-1.60 (4H, m), 1.80-1.95 (2H, m), 2.00-2.20 (2H, m), 2.70-2.84 (1H, m), 4.06-4.20 (2H, m), 4.50-4.60 (1H, m), 6.20-6.30 (2H, m), 6.86 (1H, d); m/z (ES−) 279 (M−H−).

1. customthe reaction mixture was partitioned between-ethyl-acetate (50 ml) and water (50 ml)
2. extractionThe aqueous layer was extracted with ethyl acetate (2×50 ml)
3. washThe combined organic extracts were washed with brine (50 ml)
4. dry with materialdried over magnesium sulfate
5. customevaporated in vacuo
6. dissolutionThe residue was dissolved in methanol (5 ml)
7. filtrationThe resin was filtered through a pad of celite, which
8. washwas washed well with methanol
9. concentrationThe combined filtrates were concentrated in vacuo
10. customThe residue was purified

ORD record

ord-71351d1fc43a4442b74347e8d0938489

Source dataset

uspto-grants-2004_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06797731B2