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

HRID 747392Notes

Reaction equation

HRID 747392 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].[NH2:1][C:2]1([C:7]([O:9][CH3:14])=[O:8])[CH2:6][CH2:5][CH2:4][CH2:3]1

Participants

4

Reactant 3

HCID 887MethanolHCID 2901CycloleucineHCID 24386Thionyl Chloride

Product 1

HCID 11513856Methyl 1-amino-1-cyclopentanecarboxylate, HClYield 97%

Procedure

1-Amino-1-cyclopentanecarboxylic acid (5.00 g, 38.8 mmol) was dissolved in methanol (100 mL) and then thionyl chloride (9.25 g, 77.7 mmol) was added dropwise with stirring. The resulting mixture was stirred overnight at room temperature and then concentrated in vacuo which left a white solid. The solid was tritruated in ethyl ether, filtered, and dried to give 6.78 g (97%) of methyl 1-amino-1-cyclopentanecarboxylate hydrochloride as a white solid. 1H NMR was consistent with product. ESMS (M+1) 144.2

Workup

  1. stirringThe resulting mixture was stirred overnight at room temperature
  2. concentrationconcentrated in vacuo which
  3. waitleft a white solid
  4. filtrationfiltered
  5. customdried

Sources & evidence

ORD record
ord-b01d56edbf134d5b88ac344977a51a65
Source dataset
uspto-grants-2008_07
Patent number
US07396846B2

Reaction notes

Loading…