Diisopropylethylamine → (S)-3-((S)-2-Chloro-4-hexahydro-pyrrolo[1,2-a]pyrazin-2-yl-benzenesulfonyl)-pyrrolidine-1-carboxylic acid tert-butyl ester

HRID 38047

Reaktionsgleichung

Reaktionsgleichung von HRID 38047
[Cl:1][C:2]1[CH:7]=[C:6](F)[CH:5]=[CH:4][C:3]=1[S:9]([C@H:12]1[CH2:16][CH2:15][N:14]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:13]1)(=[O:11])=[O:10].[CH2:24]1[NH:29][CH2:28][CH2:27][N:26]2[CH2:30][CH2:31][CH2:32][C@@H:25]12.CCN(C(C)C)C(C)C>C(#N)C>[C:20]([O:19][C:17]([N:14]1[CH2:15][CH2:16][C@H:12]([S:9]([C:3]2[CH:4]=[CH:5][C:6]([N:29]3[CH2:28][CH2:27][N:26]4[CH2:30][CH2:31][CH2:32][C@H:25]4[CH2:24]3)=[CH:7][C:2]=2[Cl:1])(=[O:11])=[O:10])[CH2:13]1)=[O:18])([CH3:23])([CH3:22])[CH3:21]

Komponenten

5

Edukt 3

HCID 81531DiisopropylethylamineHCID 781249(6S)-1,4-Diazabicyclo(4.3.0)nonaneHCID 67496058(S)-tert-butyl 3-(2-chloro-4-fluorophenylsulfonyl)-pyrrolidine-1-carboxylate

Produkt 1

HCID 67496771(S)-3-((S)-2-Chloro-4-hexahydro-pyrrolo[1,2-a]pyrazin-2-yl-benzenesulfonyl)-pyrrolidine-1-carboxylic acid tert-butyl esterAusbeute 96 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

In a 50 mL round-bottomed flask, (S)-tert-butyl 3-(2-chloro-4-fluorophenylsulfonyl)-pyrrolidine-1-carboxylate, example 52D) (2 g, 5.5 mmol, 1 eq) was combined with acetonitrile (20 mL) to give a light yellow solution. (S)-octahydropyrrolo[1,2-a]pyrazine (1.04 g, 8.25 mmol, 1.5 eq) and DIEA (1.42 g, 1.92 mL, 11.0 mmol, 2 eq) were added. The reaction mixture was stirred for 15 h. The reaction mixture was heated to 60° C. and stirred for 5 h. The crude reaction mixture was concentrated in vacuo. The reaction mixture was poured into EtOAc (25 mL) and extracted with aqueous 10% Na2CO3 (2×20 mL) and brine. The organic layers were dried over Na2SO4 and concentrated in vacuo to yield a colorless viscous oil (2.48 g, 96%).

Aufarbeitung

  1. customto give a light yellow solution
  2. stirringstirred for 5 h
  3. customThe crude reaction mixture
  4. concentrationwas concentrated in vacuo
  5. additionThe reaction mixture was poured into EtOAc (25 mL)
  6. extractionextracted with aqueous 10% Na2CO3 (2×20 mL) and brine
  7. dry with materialThe organic layers were dried over Na2SO4
  8. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-09e4fc306dde4c99b057c29a538b6279
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08524710B2

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