Triethylamine → rac-(3S)-1-(tert-butoxycarbonyl)-3-methyl-L-proline

HRID 1439703Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1439703
[CH2:1](N(CC)CC)C.[C:8](=[O:24])([O-])[O:9][C:10]1[CH:15]=C(Cl)C(Cl)=C(C(C)(C)C)[C:11]=1Cl.[CH3:25][C@H:26]1[CH2:30][CH2:29][NH:28][C@@H:27]1[C:31]([OH:33])=[O:32]>C(O)(C)(C)C.O>[C:10]([O:9][C:8]([N:28]1[CH2:29][CH2:30][C@H:26]([CH3:25])[C@H:27]1[C:31]([OH:33])=[O:32])=[O:24])([CH3:11])([CH3:15])[CH3:1]

Komponenten

6

Edukt 3

HCID 8471TriethylamineHCID 2724879(2S,3S)-3-methylpyrrolidine-2-carboxylic AcidHCID 86585469HCID 86585469, Verbindung

Produkt 1

HCID 22800293rac-(3S)-1-(tert-butoxycarbonyl)-3-methyl-L-proline

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6386tert-ButanolLösungsmittel

Versuchsvorschrift

Triethylamine (3.5 ml) and t-butyl-2,4,5-trichlorophenyl carbonate (3.5 g) were added to a solution of trans-3-methyl-L-proline (1.25 g) in t-butanol (12 ml) and water (8 ml). The mixture was heated to 60° for 2 hours, evaporated, the residue dissolved in 1 N sodium bicarbonate solution (50 ml) and the solution washed with ether. Excess solid citric acid was added, the product extracted into ethyl acetate, the combined extracts dried (Na2SO4) and evaporated giving a crude crystalline product (1.6 g). Recrystallisation from ethyl acetate/light petroleum (40°-60°) gave the desired product (1.33 g), m.p. 146°-150° [α]D20 - 60.1° (c, 1.0, chloroform)

Aufarbeitung

  1. temperatureThe mixture was heated to 60° for 2 hours
  2. customevaporated
  3. dissolutionthe residue dissolved in 1 N sodium bicarbonate solution (50 ml)
  4. washthe solution washed with ether
  5. additionExcess solid citric acid was added
  6. extractionthe product extracted into ethyl acetate
  7. dry with materialthe combined extracts dried (Na2SO4)
  8. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-5b069f5b73304035ac72262a2c554839
Quelldatensatz
uspto-grants-1977_11
Patentnummer
US04060603

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