Hydrochloric Acid → HCID 59253246, compound

HRID 553605Notes

Reaction equation

HRID 553605 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]

Workup

  1. concentrationThe reaction mixture is concentrated

Sources & evidence

ORD record
ord-32bde346ad2f4d1b90cfe0d4dcdcb180
Source dataset
uspto-grants-2011_11
Patent number
US08048899B2

Reaction notes

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