Hydrochloric Acid → HCID 59253246, compound

HRID 1802390Notes

Reaction equation

HRID 1802390 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH:11]([S:14][C:15]([C:18]([O:20][CH2:21][CH3:22])=[O:19])([CH3:17])[CH3:16])[CH2:10][CH2:9]1)=O)(C)(C)C.Cl>O1CCOCC1>[CH2:21]([O:20][C:18](=[O:19])[C:15]([CH3:17])([S:14][CH:11]1[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]1)[CH3:16])[CH3:22]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 59253182HCID 59253182, compound

Product 1

HCID 59253246HCID 59253246, compoundYield 105.6%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Deprotection of 6.05 g (18.3 mmol) of 4-(1-ethoxycarbonyl-1-methyl-ethylsulfanyl)-piperidine-1-carboxylic acid tert-butyl ester is achieved by treatment with 4M aqueous HCl solution (9.13 mL) in 1,4-dioxane (40 mL) at room temperature for 18 h. The reaction mixture is concentrated to afford 4.47 g of 2-methyl-2-(piperidin-4-ylsulfanyl)-propionic acid ethyl ester as its hydrochloride salt as a brown oil. Yield: 92%; ES-MS: m/z 232 [M+H]1H NMR (500 MHz, CHLOROFORM-d) δ ppm 1.21 (3 H, t, J=7.13 Hz), 1.45 (6 H, s), 1.80-1.90 (2 H, m), 2.17 (2 H, ddd, J=10.78, 7.31, 3.66 Hz), 2.96-3.05 (2 H, m), 3.07-3.15 (1 H, m), 3.18-3.30 (2 H, m), 4.09 (2 H, q, J=7.12 Hz), 9.44 (1 H, br. s.), 9.54 (1 H, br. s.)

Workup

  1. concentrationThe reaction mixture is concentrated

Sources & evidence

ORD record
ord-924b75ed9a2f4f36baa1b59efe9e73bf
Source dataset
uspto-grants-2013_01
Patent number
US08349871B2

Reaction notes

Loading…