Hydrochloric Acid → (R)-piperidin-3-yl(pyrrolidin-1-yl)methanone hydrochloride

HRID 931052Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 931052
[N:1]1([C:6]([C@@H:8]2[CH2:13][CH2:12][CH2:11][N:10](C(OC(C)(C)C)=O)[CH2:9]2)=[O:7])[CH2:5][CH2:4][CH2:3][CH2:2]1.[ClH:21].O1CCOCC1>ClCCl>[ClH:21].[NH:10]1[CH2:11][CH2:12][CH2:13][C@@H:8]([C:6]([N:1]2[CH2:2][CH2:3][CH2:4][CH2:5]2)=[O:7])[CH2:9]1

Komponenten

5

Edukt 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 28167609(R)-tert-butyl 3-(pyrrolidine-1-carbonyl)piperidine-1-carboxylate

Produkt 1

HCID 117966306(R)-piperidin-3-yl(pyrrolidin-1-yl)methanone hydrochloride

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of (R)-tert-butyl 3-(pyrrolidine-1-carbonyl)piperidine-1-carboxylate (58.82 g, 208.3 mmol) in anhydrous dichloromethane (100 mL) was added hydrogen chloride in 1,4-dioxane (260 mL, 1040 mmol, 4M). The reaction mixture was stirred vigorously at room temperature for 1 h. The solvent was removed under reduced pressure and the residue was left standing overnight at room temperature. The residue was triturated with ether (250 mL). The ether was decanted and dichloromethane was added followed by sonication in a warm bath. The solvent was removed under reduced pressure and the resulting solid was placed under high vacuum at 40° C. for 1 h to afford (R)-piperidin-3-yl(pyrrolidin-1-yl)methanone hydrochloride (48.41 g). The material was used for the next step without further purification. 1H NMR (400 MHz, CD3OD) δ 1.75-2.05 (m, 8H) 3.04-3.17 (m, 2H) 3.19-3.28 (m, 3H) 3.35-3.66 (m, 4H); MS (ES+) (M+H) 183.3.

Aufarbeitung

  1. customThe solvent was removed under reduced pressure
  2. waitthe residue was left
  3. waitstanding overnight at room temperature
  4. customThe residue was triturated with ether (250 mL)
  5. customThe ether was decanted
  6. additiondichloromethane was added
  7. customfollowed by sonication in a warm bath
  8. customThe solvent was removed under reduced pressure
  9. waitthe resulting solid was placed under high vacuum at 40° C. for 1 h

Quellen und Nachweise

ORD-Eintrag
ord-55864826b1c44afaab221eaf49dd18a7
Quelldatensatz
uspto-grants-2016_03
Patentnummer
US09296745B2

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