Methanol → (3R,6S)-1-((Benzyloxy)carbonyl)-6-methylpiperidine-3-carboxylic acid

To a stirred solution of 3-methyl 1-(phenylmethyl) (3R,6S)-6-methyl-1,3-piperidinedicarboxylate (58.9 g, 202 mmol) in THF (350 mL) at room temperature was added LiOH.H2O (10.18 g, 243 mmol, 1.2 equiv), followed by water (175 mL) and CH3OH (85 mL). The mixture was stirred at ambient temperature for 20 hours. LCMS showed complete hydrolysis. The mixture was concentrated in vacuo. The residue was taken up in EtOAc (500 mL), acidified with 120 mL of cold 2N HCl, and diluted with 200 mL of brine. The phases were separated. The aqueous phase was extracted with EtOAc (2×300 mL). The combined organic was dried over Na2SO4, filtered, and concentrated in vacuo to give the title compound (57 g) as an oil. LC-MS (ES) m/z=278 [M+H]+.

1. customhydrolysis
2. concentrationThe mixture was concentrated in vacuo
3. additiondiluted with 200 mL of brine
4. customThe phases were separated
5. extractionThe aqueous phase was extracted with EtOAc (2×300 mL)
6. dry with materialThe combined organic was dried over Na2SO4
7. filtrationfiltered
8. concentrationconcentrated in vacuo

ORDレコード

ord-3d1641f16ec5447f8a6f115413e87bb2

出典データセット

uspto-grants-2014_04

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US08697685B2