Hydrochloric Acid → 2-(Pyrrolidin-1-yl)acetic acid hydrochloride

HRID 11246

Reaktionsgleichung

Reaktionsgleichung von HRID 11246
Br[CH2:2][C:3]([O:5]C(C)(C)C)=[O:4].[NH:10]1[CH2:14][CH2:13][CH2:12][CH2:11]1.[ClH:15]>C1COCC1.O1CCOCC1>[ClH:15].[N:10]1([CH2:2][C:3]([OH:5])=[O:4])[CH2:14][CH2:13][CH2:12][CH2:11]1

Komponenten

6

Edukt 3

HCID 313Hydrochloric AcidHCID 31268PyrrolidineHCID 79177tert-Butyl bromoacetate

Produkt 1

HCID 130220162-(Pyrrolidin-1-yl)acetic acid hydrochlorideAusbeute 97,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittel2×HCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

A solution of 19.6 grams (101 mmol) of t-butyl bromoacetate in 150 mL of THF was cooled in an ice bath and treated dropwise over about 0.5 hour with a solution of 14.4 grams (202 mmol) of pyrrolidine in 75 mL of THF, to produce a white precipitate. The bath was removed and the reaction slurry stirred for two hours. The solid was removed by filtration and the filtrate was concentrated under reduced pressure to yield a clear liquid over an orange-colored solid. The liquid was cooled in an ice bath, then treated with 40 mL (80 mmol) of 4N HCl in dioxane and stirred for 15 hours. The solvents were removed in vacuo, and the residue was triturated with diethyl ether, then filtered to yield 12.9 grams of the desired acid as an off-white solid.

Aufarbeitung

  1. customto produce a white precipitate
  2. customThe bath was removed
  3. customThe solid was removed by filtration
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. customto yield a clear liquid over an orange-colored solid
  6. temperatureThe liquid was cooled in an ice bath
  7. stirringstirred for 15 hours
  8. customThe solvents were removed in vacuo
  9. customthe residue was triturated with diethyl ether
  10. filtrationfiltered

Quellen und Nachweise

ORD-Eintrag
ord-0ae0c5722f76466c92866d5ed37fa793
Quelldatensatz
uspto-grants-2006_08
Patentnummer
US07098202B2

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