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

HRID 1767294Notes

Reaction equation

HRID 1767294 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-d2aa863e8eec417ba3aa6e9fe4a88ffe
Source dataset
uspto-grants-2007_06
Patent number
US07232924B2

Reaction notes

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