Hydrochloric Acid → Rac-(1r,3r)-3-(dimethylamino)cyclobutane-1-carboxylic acid hydrochloride

HRID 626568Notes

Reaction equation

HRID 626568 reaction equation
[CH3:1][N:2]([CH3:11])[CH:3]1[CH2:6][CH:5]([C:7]([O:9]C)=[O:8])[CH2:4]1.[ClH:12]>O1CCOCC1>[ClH:12].[CH3:1][N:2]([CH3:11])[CH:3]1[CH2:6][CH:5]([C:7]([OH:9])=[O:8])[CH2:4]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 90410277Methyl 3-(dimethylamino)cyclobutanecarboxylate

Product 1

HCID 90411221Rac-(1r,3r)-3-(dimethylamino)cyclobutane-1-carboxylic acid hydrochlorideYield 101%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
70 °C

Procedure

A solution of methyl 3-(dimethylamino)cyclobutanecarboxylate (0.596 g, 3.79 mmol) in dioxane (5 mL) was treated with HCl (6N, 10 mL, 60 mmol) and heated at 70° C. overnight. The organics were removed under reduced pressure and the aqueous residue was treated with MeCN, frozen and lyophilized to afford 3-(dimethylamino)cyclobutanecarboxylic acid hydrochloride (686 mg, 101%). 1H NMR (400 MHz, DMSO-d6): δ 10.86 (br s, 1H), 3.56-3.48 (m, 1H), 2.83-2.73 (m, 1H), 2.58 (d, J=4.9 Hz, 6H), 2.41-2.33 (m, 4H).

Workup

  1. customThe organics were removed under reduced pressure
  2. additionthe aqueous residue was treated with MeCN
  3. temperaturefrozen

Sources & evidence

ORD record
ord-819af13b42444f9d83d4a2e784246d98
Source dataset
uspto-grants-2016_04
Patent number
US09309224B2

Reaction notes

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