Methanol → Methyl 1-aminocyclobutane-1-carboxylate hydrochloride

HRID 1519076Notes

Reaction equation

HRID 1519076 reaction equation
Cl.[NH2:2][C:3]1([C:7]([OH:9])=[O:8])[CH2:6][CH2:5][CH2:4]1.S(Cl)([Cl:12])=O.[CH3:14]O>>[ClH:12].[CH3:14][O:8][C:7]([C:3]1([NH2:2])[CH2:6][CH2:5][CH2:4]1)=[O:9]

Participants

4

Reactant 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 113210481-Aminocyclobutanecarboxylic Acid Hydrochloride

Product 1

HCID 42614147Methyl 1-aminocyclobutane-1-carboxylate hydrochlorideYield 98%

Procedure

1-aminocyclobutanecarboxylic acid hydrochloride (5.2 g, 34.5 mmol) and methanol (120 ml) were charged. An ice bath was set, and thionyl chloride (3.7 ml, 51.7 mmol) was slowly added thereto. Then, the ice bath was removed, and the mixture was stirred at room temperature for 3 hours. The resultant product was vacuum-distilled to remove a solvent, and dried in a 60° C. oven so as to obtain methyl-1-aminocyclobutanecarboxylate hydrochloride (5.62 g, 37.1 mmol, 98%).

Workup

  1. customAn ice bath was set
  2. customThen, the ice bath was removed
  3. distillationThe resultant product was vacuum-distilled
  4. customto remove a solvent
  5. customdried in a 60° C. oven so as

Sources & evidence

ORD record
ord-193666d36c104a09851d47529f1a1295
Source dataset
uspto-grants-2015_07
Patent number
US09073830B2

Reaction notes

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