Hydrochloric Acid → HCID 69515936, compound

HRID 1796826Notes

Reaction equation

HRID 1796826 reaction equation
C(OC([NH:8][CH2:9][C:10]1([C:16]([OH:18])=[O:17])[CH2:12][CH:11]1[CH:13]([CH3:15])[CH3:14])=O)(C)(C)C.[ClH:19].CCOCC>O1CCOCC1>[ClH:19].[NH2:8][CH2:9][C:10]1([C:16]([OH:18])=[O:17])[CH2:12][CH:11]1[CH:13]([CH3:15])[CH3:14]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 22182729HCID 22182729, compound

Product 1

HCID 69515936HCID 69515936, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a solution of 1-(tert-butoxycarbonylamino-methyl)-2-isopropyl-cyclopropanecarboxylic acid (2.05 g, 8.0 mmol) in dry 1,4-dioxane (40 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-aminomethyl-2-isopropyl-cyclopropanecarboxylic acid hydrochloride (1.35 g, 88%): mp: 245–246° C.; 1H NMR (300 MHz, D2O) δ 0.94 (d, J=6.5 Hz, 3H), 0.96 (m, 1H), 1.05 (d, J=6.4 Hz, 3H), 1.23–1.31 (m, 1H), 1.49–1.59 (m, 2H), 2.85 (d, J=13.7 Hz, 1H), 3.83 (d, J=13.7 Hz, 1H); 13C NMR (75 MHz, D2O) δ 22.3, 23.9, 27.8, 30.8, 39.6, 41.7, 179.6; MS (APCI) m/z 158 [M+H]+. Anal. Calcd. For C8H15NO2—HCl: C, 49.61; H, 8.33; N, 7.23; Cl, 18.31. Found: C, 49.76; H, 8.44; N, 7.11; Cl, 18.48.

Workup

  1. customThe white solid was collected
  2. customdried

Sources & evidence

ORD record
ord-1a276bd8de5e40e892b9b392e8361d6f
Source dataset
uspto-grants-2006_04
Patent number
US07030267B2

Reaction notes

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