Lithium hydroxide, monohydrate → HCID 10241207, compound

HRID 1796835Notes

Reaction equation

HRID 1796835 reaction equation
C[O:2][C:3]([C:5]1([CH2:12][NH2:13])[C:7]2([CH2:11][CH2:10][CH2:9][CH2:8]2)[CH2:6]1)=[O:4].O[Li].O>CO>[NH2:13][CH2:12][C:5]1([C:3]([OH:4])=[O:2])[C:7]2([CH2:11][CH2:10][CH2:9][CH2:8]2)[CH2:6]1

Participants

4

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 11298342Methyl 1-(aminomethyl)spiro[2.4]heptane-1-carboxylate

Product 1

HCID 10241207HCID 10241207, compoundYield 39%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 1-aminomethyl-spiro[2.4]heptane-1-carboxylic acid methyl ester (3.40 g, 18.6 mmol) was added methanol (75 mL) and LiOH—H2O (1.55 g, 37.1 mmol). The mixture was heated to reflux under nitrogen for 48 hours. The solvent was removed by evaporation under reduced pressure and the residue was dissolved in water (50 mL). With ice bath cooling, concentrated HCl (˜2.5 mL) was added until the pH was adjusted to 6. A white precipitate was isolated by filtration and dried under vacuum to yield 1.22 g (39%) of 1-aminomethyl-spiro[2.4]heptane-1-carboxylic acid as an off-white solid: mp 231–235° C. (decomposition); 1H NMR (300 MHz, D2O) δ 0.78 (d, J=4.7 Hz, 1H), 1.32 (d, J=4.7 Hz, 1H), 1.40 (m, 1H), 1.54–1.77 (m, 7H), 2.86 (d, J=13.2 Hz, 1H), 3.43 (d, J=13.2 Hz, 1H); MS (APCI) m/z 170 [M+H]+. Anal. Calcd. For C9H15NO2 −1.1H2O: C, 57.18; H, 9.17; N, 7.41. Found: C, 57.38; H, 8.82; N, 7.09.

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux under nitrogen for 48 hours
  3. customThe solvent was removed by evaporation under reduced pressure
  4. dissolutionthe residue was dissolved in water (50 mL)
  5. temperatureWith ice bath cooling
  6. additionconcentrated HCl (˜2.5 mL) was added until the pH
  7. customA white precipitate was isolated by filtration
  8. customdried under vacuum

Sources & evidence

ORD record
ord-b598994c3b894d448100cbc73debb372
Source dataset
uspto-grants-2006_04
Patent number
US07030267B2

Reaction notes

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