Water → HCID 86707789, compound

To a solution of 3-(4-Diethoxymethyl-phenyl)-3-hydroxy-cyclobutanecarboxylic acid ethyl ester (Preparation 1, 7 g, 21.73 mmol) in EtOH:H2O (80 mL, 1:1) was added sodium acetate (3.2 g, 39.31 mmol) followed by hydroxylamine hydrochloride (2.24 g, 32.60 mmol) at 0° C. Resulting reaction mixture was stirred at room temperature for 16 hours. After consumption of starting material, reaction mixture was concentrated in vacuo and diluted with water (70 mL). Aqueous layer was extracted with EtOAc (3×70 mL). Combined organic layer was dried over sodium sulphate, filtered and evaporated under reduced pressure to afford crude residue. Crude was purified by column chromatography on silica gel (100-200 mesh size). Compound was eluted using 40% ethyl acetate in hexane to afford yellowish oil (4.7 g, 87%). 1H NMR and LC-MS was consistent. 1H NMR (400 MHz, DMSO-d6) δ: 1.19 (t, J=7.16 Hz, 3H), 2.60-2.65 (m, 2H), 2.78-2.82 (m, 1H), 4.07 (q, J=7.1 Hz, 2H), 7.50-7.50 (m, 4H), 8.12 (s, 1H), 11.18 (s, 1H). LCMS (m/z): 246.10 (M+H).

1. customResulting
2. customreaction mixture
3. customAfter consumption of starting material, reaction mixture
4. concentrationwas concentrated in vacuo
5. additiondiluted with water (70 mL)
6. extractionAqueous layer was extracted with EtOAc (3×70 mL)
7. dry with materialCombined organic layer was dried over sodium sulphate
8. filtrationfiltered
9. customevaporated under reduced pressure
10. customto afford crude residue
11. customCrude was purified by column chromatography on silica gel (100-200 mesh size)
12. washCompound was eluted

ORD record

ord-7632b4725a07463aa06d1ef07952c363

Source dataset

uspto-grants-2015_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09061013B2