Hydrochloric Acid → 1-Aminomethyl-2-isobutyl-cyclopropanecarboxylic acid hydrochloride

HRID 1297237Notes

Reaction equation

HRID 1297237 reaction equation
C(OC([NH:8][CH2:9][C:10]1([C:17]([OH:19])=[O:18])[CH2:12][CH:11]1[CH2:13][CH:14]([CH3:16])[CH3:15])=O)(C)(C)C.[ClH:20].CCOCC>O1CCOCC1>[ClH:20].[NH2:8][CH2:9][C:10]1([C:17]([OH:19])=[O:18])[CH2:12][CH:11]1[CH2:13][CH:14]([CH3:16])[CH3:15]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 221827451-(Tert-butoxycarbonylamino-methyl)-2-isobutyl-cyclopropanecarboxylic acid

Product 1

HCID 695158221-Aminomethyl-2-isobutyl-cyclopropanecarboxylic acid hydrochlorideYield 76%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a solution of 1-(tert-butoxycarbonylamino-methyl)-2-isobutyl-cyclopropanecarboxylic acid (2.8 g, 10.3 mmol) in dry 1,4-dioxane (60 mL) was added 4N HCl (40 mL, in 1,4-dioxane). The reaction mixture was stirred at room temperature overnight and ether was added (100 mL). The white solid was collected and dried to give 1.6 g (76%) of 1-aminomethyl-2-isobutyl-cyclopropanecarboxylic acid hydrochloride: mp: 254-255° C.; 1H NMR (300 MHz, D2O) δ 0.95(t, J=6.2 Hz, 6H), 0.96 (m, 1H), 1.21-1.28 (m, 1H), 1.51-1.80 (m, 4H), 3.06 (d, J=13.8 Hz, 1H), 3.58 (d, J=13.8 Hz, 1H); 13C NMR (75 MHz, D2O) δ 21.7, 21.9, 22.2, 25.3, 28.1, 28.6, 37.1, 40.2, 178.1; MS (APCI) m/z 172 [M+H]+. Anal. Calc'd For C9H17NO2—HCl: C, 52.05; H, 8.74; N, 6.74. Found: C, 52.10; H, 8.73; N, 6.67.

Workup

  1. customThe white solid was collected
  2. customdried

Sources & evidence

ORD record
ord-2350472654c24816a07a4454e77ad051
Source dataset
uspto-grants-2007_07
Patent number
US07250433B2

Reaction notes

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