Hydrochloric Acid → 2-Aminomethyl-4,4-dimethyl-heptanoic acid hydrochloride

HRID 2216675Notes

Reaction equation

HRID 2216675 reaction equation
C([O:3][C:4](=[O:15])[C:5]([C:13]#[N:14])=[CH:6][C:7]([CH3:12])([CH3:11])[CH2:8][CH:9]=[CH2:10])C.[H][H].[ClH:18]>C(O)C.O=[Pt]=O>[ClH:18].[NH2:14][CH2:13][CH:5]([CH2:6][C:7]([CH3:11])([CH3:12])[CH2:8][CH2:9][CH3:10])[C:4]([OH:15])=[O:3]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 858712602-Cyano-4,4-dimethyl-hepta-2,6-dienoic acid ethyl esterHCID 178418361HCID 178418361, compound

Product 1

HCID 713740332-Aminomethyl-4,4-dimethyl-heptanoic acid hydrochloride

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 702EthanolSolvent

Procedure

2-Cyano-4,4-dimethyl-hepta-2,6-dienoic acid ethyl ester (5.88 g, 28 mmol) was dissolved in the mixture of 91 mL of ethanol and 6 mL of HCl and treated with 0.4 g of PtO2. The reaction was carried out under 100 psi of hydrogen pressure at room temperature for 15 hours. The catalyst was filtered and filtrate was concentrated to give 3.8 g of the desired product 2-aminomethyl-4,4-dimethyl-heptanoic acid ethyl ester as an oil. MS (APCI): 216.2 (M+1)+. This oil was refluxed in 75 mL of 6N HCl for 18 hours. While the reaction was cooled, a precipitate formed. The solid was filtered, washed with additional HCl solution and triturated with ether to give the clean title compound. MS (APCI): 188.1 (M+1)+. 186.1 (M−1)+. 1H NMR (400 MHz; CD3OD): 0.91 (9H, m), 1.30 (5H, m), 1.81 (dd, 1H, J=7.2 Hz, 14.4 Hz), 2.72 (1H, m), 3.04 (2H, m); Anal. Calc'd for C10H21NO2.HCl: C, 53.68; H, 9.91; N, 6.26; Cl, 15.85; Found: C: 53.83; H, 10.15; N, 6.22; Cl, 15.40. MP: 229.5–231.0° C.

Workup

  1. filtrationThe catalyst was filtered
  2. concentrationfiltrate was concentrated

Sources & evidence

ORD record
ord-ba67975cda624382ab7e17c55fc0ae94
Source dataset
uspto-grants-2006_09
Patent number
US07112610B2

Reaction notes

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