Methanol → methyl (1S,3R)-3-aminocyclopentane-1-carboxylate hydrochloride

HRID 2234361Notes

Reaction equation

HRID 2234361 reaction equation
[NH2:1][C@@H:2]1[CH2:6][CH2:5][C@H:4]([C:7]([OH:9])=[O:8])[CH2:3]1.S(Cl)([Cl:12])=O.[CH3:14]O>>[ClH:12].[NH2:1][C@@H:2]1[CH2:6][CH2:5][C@H:4]([C:7]([O:9][CH3:14])=[O:8])[CH2:3]1

Participants

4

Reactant 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 15020343-Aminocyclopentane-1-carboxylic acid

Product 1

HCID 66933126methyl (1S,3R)-3-aminocyclopentane-1-carboxylate hydrochloride

Procedure

(1S,3R)-3-aminocyclopentane-1-carboxylic acid (Acros; 952 mg, 7.37 mmol) was suspended in MeOH (15 ml) and cooled in an acetone/ice bath. Thionyl chloride (1.11 mL, 14.74 mmol) was added dropwise and the resulting pale yellow solution stirred in the acetone/ice bath for 30 minutes and then allowed to warm to room temperature, stirred at room temperature for 1 hr then heated at reflux for 1 hr. Solvents were evaporated to give the title compound as a cream solid after drying under high vacuum. (1.32 g 100%)

Workup

  1. temperaturecooled in an acetone/ice bath
  2. temperaturethen heated
  3. temperatureat reflux for 1 hr
  4. customSolvents were evaporated

Sources & evidence

ORD record
ord-1126e28375ef4c69ab5ed1c7633229fb
Source dataset
uspto-grants-2010_05
Patent number
US07709471B2

Reaction notes

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