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Tetrahydrofuran → (S)-4-(t-Butyldimethylsilyloxy)pyrrolidin-2-one

HRID 1632096
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1632096
[C:1]([Si:5]([CH3:32])([CH3:31])[O:6][C@@H:7]1[CH2:11][N:10](CC2C=C(C3C=CC=C([N+]([O-])=O)C=3)C(OC)=CC=2)[C:9](=[O:30])[CH2:8]1)([CH3:4])([CH3:3])[CH3:2].C1COCC1.[H-].[Na+]>O>[C:1]([Si:5]([CH3:32])([CH3:31])[O:6][C@@H:7]1[CH2:11][NH:10][C:9](=[O:30])[CH2:8]1)([CH3:4])([CH3:3])[CH3:2]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 8028TetrahydrofuranHCID 24758Sodium hydrideHCID 58019967(S)-4-(tert-Butyl-dimethyl-silanyloxy)-1-(6-methoxy-3'-nitro-biphenyl-3-ylmethyl)-pyrrolidin-2-one

Produkt 1

HCID 11074789(S)-4-(t-Butyldimethylsilyloxy)pyrrolidin-2-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

Synthesis of ((S)-4-(tert-Butyl-dimethyl-silanyloxy)-1-(6-methoxy-3′-nitro-biphenyl-3-ylmethyl)-pyrrolidin-2-one (I-213). Into a 250 mL round-bottomed flask with a stir bar was added I-212 (2.57 g, 11.95 mmol), THF (150 mL), and the solution was cooled to 0° C. NaH (0.56 g, 14.12 mmol) was added and the suspension was stirred at room temperature for 30 minutes. To this, I-70 (3.50 g, 10.86 mmol) was added and the reaction was stirred for 20 hours at room temperature after which time 50 mL of water was added and the product was extracted with ethyl acetate. The organics were concentrated to yield 8.9 g of I-213, which was used as is in the next reaction.

Aufarbeitung

  1. additionInto a 250 mL round-bottomed flask with a stir bar was added
  2. additionTo this, I-70 (3.50 g, 10.86 mmol) was added
  3. additionwas added
  4. extractionthe product was extracted with ethyl acetate
  5. concentrationThe organics were concentrated
  6. customto yield 8.9 g of I-213, which
  7. customas is in the next reaction

Quellen und Nachweise

ORD-Eintrag
ord-c1d75640d30b47caaa676d0b7f2aad6b
Quelldatensatz
uspto-grants-2014_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08791267B2

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