Triethylamine → 2-[2-(1-methoxycarbonyl-(S)-ethylamino)-ethyl]-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester

HRID 1441719Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1441719
[CH3:1][O:2][C:3]([C:5]1([CH2:17][CH:18]=O)[CH2:9][CH2:8][CH2:7][N:6]1[C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])=[O:4].Cl.[CH3:21][O:22][C:23](=[O:27])[C@H:24]([CH3:26])[NH2:25].C(N(CC)CC)C.C([BH3-])#N.[Na+]>C1(C)C=CC=CC=1.CO>[CH3:1][O:2][C:3]([C:5]1([CH2:17][CH2:18][NH:25][C@H:24]([C:23]([O:22][CH3:21])=[O:27])[CH3:26])[CH2:9][CH2:8][CH2:7][N:6]1[C:10]([O:12][C:13]([CH3:14])([CH3:15])[CH3:16])=[O:11])=[O:4]

Komponenten

7

Edukt 4

HCID 8471TriethylamineHCID 2733257Alanine methyl ester hydrochlorideHCID 5003444Sodium cyanoborohydrideHCID 738300911-Tert-butyl 2-methyl 2-(2-oxoethyl)pyrrolidine-1,2-dicarboxylate

Produkt 1

HCID 686800982-[2-(1-methoxycarbonyl-(S)-ethylamino)-ethyl]-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 1140TolueneLösungsmittel

Versuchsvorschrift

271 mg (1 mmol) 2-(2-oxo-ethyl)-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester and 154 mg (1.1 mmol) L-alanine methyl ester hydrochloride are suspended in 10 mL toluene and treated with 0.073 mL (1 eq.) triethylamine. The reaction mixture is stirred 10 minutes at room temperature and slowly evaporated in a rotary evaporator. The residue is taken up in 15 mL acetonitrile and 95 mg (1.5 mmol) sodium cyanoborohydride in 2 mL methanol added dropwise. Upon completion of the reaction (TLC, EtOAc/petroleum ether 4:1), the reaction mixture is evaporated and the residue taken up in ethyl acetate and treated with an ice-cold, saturated aqueous ammonium chloride solution, then extracted with ethyl acetate and saturated aqueous sodium bicarbonate. The combined organic phases are dried over sodium sulfate, filtered and evaporated to yield the crude desired product as a thick oil.

Aufarbeitung

  1. customslowly evaporated in a rotary evaporator
  2. customthe reaction mixture is evaporated
  3. additiontreated with an ice-cold, saturated aqueous ammonium chloride solution
  4. extractionextracted with ethyl acetate and saturated aqueous sodium bicarbonate
  5. dry with materialThe combined organic phases are dried over sodium sulfate
  6. filtrationfiltered
  7. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-dcea2c0cb6b8418eb7fa0a18b9e7af1a
Quelldatensatz
uspto-grants-2010_02
Patentnummer
US07655686B2

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