Methanol → Methyl 1-amino-1-cyclopentanecarboxylate, HCl

HRID 1519083Notes

Reaction equation

HRID 1519083 reaction equation
[NH2:1][C:2]1([C:7]([OH:9])=[O:8])[CH2:6][CH2:5][CH2:4][CH2:3]1.S(Cl)([Cl:12])=O.[CH3:14]O>>[ClH:12].[CH3:14][O:8][C:7]([C:2]1([NH2:1])[CH2:6][CH2:5][CH2:4][CH2:3]1)=[O:9]

Participants

4

Reactant 3

HCID 887MethanolHCID 2901CycloleucineHCID 24386Thionyl Chloride

Product 1

HCID 11513856Methyl 1-amino-1-cyclopentanecarboxylate, HClYield 98%

Procedure

1-aminocyclopentanecarboxylic acid (3.5 g, 26.9 mmol) and methanol (100 ml) were charged. An ice bath was set and thionyl chloride (3.9 ml, 53.9 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-aminocyclopentanecarboxylate hydrochloride (4.74 g, 26.4 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-1444f92add46461aac8f62f1099a5db6
Source dataset
uspto-grants-2015_07
Patent number
US09073830B2

Reaction notes

Loading…