Hydrochloric Acid → Benzyl 3-(aminomethyl)-5-methylhexanoate hydrochloride

HRID 30523Notes

Reaction equation

HRID 30523 reaction equation
C(OC([NH:8][CH2:9][CH:10]([CH2:22][CH:23]([CH3:25])[CH3:24])[CH2:11][C:12]([O:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[O:13])=O)(C)(C)C.[ClH:26]>O1CCOCC1>[ClH:26].[NH2:8][CH2:9][CH:10]([CH2:22][CH:23]([CH3:25])[CH3:24])[CH2:11][C:12]([O:14][CH2:15][C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1)=[O:13]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 21113527Benzyl 3-[(tert-Butoxycarbonyl)aminomethyl]-5-Methyl-Hexanoate

Product 1

HCID 21113525Benzyl 3-(aminomethyl)-5-methylhexanoate hydrochlorideYield 88%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A solution of (38) (1.77 g, 4.78 mmol) in 4M HCl in dioxane (20 mL) was stirred at ambient temperature for 30 min. Removal of the solvent in vacuo afforded the title compound (39) as a white crystalline solid (1.4 g, 88%). 1H—NMR (CDCl3, 400 MHz): δ 0.85 (d, 6H), 1.17 (m, 1H), 1.30 (m, 1H), 1.58 (m, 1H), 2.32 (m, 1H), 2.57 (m, 2H), 3.03 (m, 2H), 5.09 (s, 2H), 7.30 (m, 5H), 8.39 (br.s, 3H). MS (ESI) m/z 250.25 (M+H+).

Workup

  1. customRemoval of the solvent in vacuo

Sources & evidence

ORD record
ord-63b59c0d9a6d47c2995d406d780d61fa
Source dataset
uspto-grants-2008_09
Patent number
US07423169B2

Reaction notes

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