Dimethylformamide → 1,3-Dibenzyl (3RS,4SR)-3-[2-(tert-butoxy)-2-oxoethyl]-4-methylpyrrolidine-1,3-dicarboxylate

HRID 446034Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 446034
[CH2:1](Br)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:9]([O:16][C:17]([N:19]1[CH2:23][CH:22]([CH3:24])[C:21]([CH2:28][C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])([C:25]([OH:27])=[O:26])[CH2:20]1)=[O:18])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.C(=O)([O-])[O-].[K+].[K+].CN(C)C=O>O>[C:32]([O:31][C:29](=[O:30])[CH2:28][C:21]1([C:25]([O:27][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[O:26])[CH:22]([CH3:24])[CH2:23][N:19]([C:17]([O:16][CH2:9][C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=2)=[O:18])[CH2:20]1)([CH3:34])([CH3:33])[CH3:35]

Komponenten

6

Edukt 4

HCID 6228DimethylformamideHCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 71293735(3RS,4SR)-1-[(Benzyloxy)carbonyl]-3-[2-(tert-butoxy)-2-oxoethyl]-4-methylpyrrolidine-3-carboxylic acid

Produkt 1

HCID 866782511,3-Dibenzyl (3RS,4SR)-3-[2-(tert-butoxy)-2-oxoethyl]-4-methylpyrrolidine-1,3-dicarboxylateAusbeute 98,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
5 °C

Versuchsvorschrift

Benzyl bromide (4.48 ml, 37.7 mmol) was added to a mixture of (3RS,4SR)-1-[(benzyloxy)carbonyl]-3-[2-(tert-butoxy)-2-oxoethyl]-4-methylpyrrolidine-3-carboxylic acid obtained in Reference Example 1b (14.5 g, 38.5 mmol), potassium carbonate (10.6 g, 77 mmol) and N,N-dimethylformamide (50 ml) with stirring under ice-cooling (internal temperature: 3 to 7° C.), and the mixture was stirred for one hour, returned to mom temperature and stirred overnight. Water was added to the reaction liquid, which was extracted with ethyl acetate three times. The organic layers were combined, sequentially washed with a saturated aqueous ammonium chloride solution (five times), water (twice) and brine, and then dried over sodium sulfate, filtered and concentrated to give the title compound (17.67 g, yield: 98.2%).

Aufarbeitung

  1. stirringthe mixture was stirred for one hour
  2. stirringstirred overnight
  3. extractionwas extracted with ethyl acetate three times
  4. washsequentially washed with a saturated aqueous ammonium chloride solution (five times), water (twice) and brine
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-d09bee670b6d48cfb1eafed9b9e09818
Quelldatensatz
uspto-grants-2013_07
Patentnummer
US08476301B2

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