Hydrochloric Acid → tert-Butyl 3-sulfanylpyrrolidine-1-carboxylate

HRID 2239563Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2239563
C([S:4][CH:5]1[CH2:9][CH2:8][N:7]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:6]1)(=O)C.C[S-].[Na+].Cl>CO>[SH:4][CH:5]1[CH2:9][CH2:8][N:7]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:6]1

Komponenten

5

Edukt 3

HCID 313Hydrochloric AcidHCID 4378561Sodium methanethiolateHCID 54776232tert-Butyl 3-(acetylthio)pyrrolidine-1-carboxylate

Produkt 1

HCID 13324658tert-Butyl 3-sulfanylpyrrolidine-1-carboxylateAusbeute 99 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

tert-Butyl 3-(acetylthio)pyrrolidine-1-carboxylate (200 mg, 0.81 mmol) was dissolved in MeOH (10mL) and sodium methanethiolate (57 mg, 0.81 mmol) was added. The reaction mixture was stirred at rt for 30 mins. HCl (1M solution) was added and the aqueous layer extracted with DCM. The organic layer was washed with brine, dried (Na2SO4), filtered and evaporated affording the title compound (0.163 g, 98.4%). 1H NMR (500 MHz, CDCl3): δ 1.44 (s, 9H), 1.68 (d, 1H), 1.75-1.84 (m, 1H), 2.22-2.28 (m, 1H), 3.13-3.23 (m, 1H), 3.30-3.40 (m, 2H), 3.47-3.57 (m, 1H), 3.67-3.74 (m, 1H).

Aufarbeitung

  1. extractionthe aqueous layer extracted with DCM
  2. washThe organic layer was washed with brine
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-41b14c9d5fa94d7999adc86c6e9f609b
Quelldatensatz
uspto-grants-2010_05
Patentnummer
US07723333B2

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