TERT-BUTYL 3-FLUORO-4-OXOPIPERIDINE-1-CARBOXYLATE → Hydrochloric Acid

HRID 2406237Notes

Reaction equation

HRID 2406237 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][C:11](=[O:14])[CH:10]([F:15])[CH2:9]1)=O)(C)(C)C.O1CCOCC1.[ClH:22]>>[F:15][CH:10]1[C:11](=[O:14])[CH2:12][CH2:13][NH:8][CH2:9]1.[ClH:22]

Participants

4

Reactant 2

HCID 10560711TERT-BUTYL 3-FLUORO-4-OXOPIPERIDINE-1-CARBOXYLATEHCID 204431481,4-Dioxane hydrochloride

Product 2

HCID 313Hydrochloric AcidHCID 252105113-Fluoropiperidin-4-one

Procedure

3-Fluoro-4-oxo-piperidine-1-carboxylic acid tert-butyl ester (2.7 g, 12.4 mmol) was dissolved in dioxane/HCl (100 mL, 0.12 M) and stirred at ambient temperature for 2 hours. Volatiles were then removed in vacuo to afford 3-fluoro-piperidin-4-one as an HCl salt, which was carried on without further purification (1.7 g, 92% yield). 1H NMR (400 MHz, DMSO-d6) δ ppm 9.77 (br. s., 1H), 8.77 (br. s., 1H), 6.36 (br. s., 2H), 4.41-4.53 (d, J=48 Hz, 1H), 3.37 (t, J=9.85 Hz, 1H), 3.21 (m, 1H), 3.08 (m, 1H), 2.93 (m, 1H), 1.94 (m, 1H), 1.77 (m, 1H).

Workup

  1. customVolatiles were then removed in vacuo

Sources & evidence

ORD record
ord-072d3196aa6a4a8cafc4a089011fcab4
Source dataset
uspto-grants-2014_08
Patent number
US08809352B2

Reaction notes

Loading…