Methanol → (1R,3S)-methyl 3-aminocyclopentanecarboxylate

HRID 2176933Notes

Reaction equation

HRID 2176933 reaction equation
S(Cl)(Cl)=O.[NH2:5][C@H:6]1[CH2:10][CH2:9][C@@H:8]([C:11]([OH:13])=[O:12])[CH2:7]1.[CH3:14]O>>[NH2:5][C@H:6]1[CH2:10][CH2:9][C@@H:8]([C:11]([O:13][CH3:14])=[O:12])[CH2:7]1

Participants

4

Reactant 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 150203549805-32-5

Product 1

HCID 10464431(1R,3S)-methyl 3-aminocyclopentanecarboxylateYield 87%

Procedure

Thionyl chloride (1.30 ml, 18.2 mmol) was added to a stirred solution of (1R,3S)-3-amino cyclo pentyl carboxylic acid (2.00 g, 12.1 mmol) in MeOH (20 ml) and refluxed for 3 h. The reaction mixture was concentrated under reduced pressure and co-distilled with toluene to afford 1.9 g (87%) of (1R,3S)-methyl 3-aminocyclopentanecarboxylate as off-white solid.

Workup

  1. temperaturerefluxed for 3 h
  2. concentrationThe reaction mixture was concentrated under reduced pressure and co-distilled with toluene

Sources & evidence

ORD record
ord-d5ad27b3b46b46dc936e27b74c2d7096
Source dataset
uspto-grants-2015_06
Patent number
US09067888B2

Reaction notes

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