Hydrochloric Acid → HCID 9942501, compound

HRID 983686Notes

Reaction equation

HRID 983686 reaction equation
C[O:2][C:3](=[O:17])[CH2:4][C@@:5]1([CH2:11][NH:12]C(OC)=O)[CH2:9][CH2:8][C@@H:7]([CH3:10])[CH2:6]1.[ClH:18]>O1CCOCC1.O>[ClH:18].[NH2:12][CH2:11][C@:5]1([CH2:4][C:3]([OH:17])=[O:2])[CH2:9][CH2:8][C@@H:7]([CH3:10])[CH2:6]1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 58626992HCID 58626992, compound

Product 1

HCID 9942501HCID 9942501, compoundYield 25%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

[(1R,3R)-1-(Methoxycarbonylamino-methyl)-3-methyl-cyclopentyl]-acetic acid methyl ester (2.60 g, 37 mmol) was refluxed in a mixture of 1,4-dioxane (15 mL) and 6N Hydrochloric acid (30 mL) for 16 hours. The mixture was allowed to cool, diluted with water (80 mL), and washed with dichloromethane (2×200 mL). The aqueous layer was evaporated under reduced pressure, and the residue was recrystallized from ethyl acetate/methanol (95:5) to give 0.55 g (25%) of ((1R,3R)-1-aminomethyl-3-methyl-cyclopentyl)-acetic acid hydrochloride;

Workup

  1. temperatureto cool
  2. washwashed with dichloromethane (2×200 mL)
  3. customThe aqueous layer was evaporated under reduced pressure
  4. customthe residue was recrystallized from ethyl acetate/methanol (95:5)

Sources & evidence

ORD record
ord-5a973e41b7d943a9bb6ee1b000baae82
Source dataset
uspto-grants-2005_03
Patent number
US06864390B2

Reaction notes

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