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Trimethylsilyldiazomethane → methyl 2-(tert-butoxy)-2-(6-methyl-7-oxo-4-(p-tolyl)-6,7-dihydro-1H-pyrrolo[2,3-c]pyridin-5-yl)acetate

HRID 1473223
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1473223
C([N:8]1[C:12]2[C:13](=[O:34])[N:14]([CH3:33])[C:15]([CH:24]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])[C:25]([OH:27])=[O:26])=[C:16]([C:17]3[CH:22]=[CH:21][C:20]([CH3:23])=[CH:19][CH:18]=3)[C:11]=2[CH:10]=[CH:9]1)C1C=CC=CC=1.[Li+].[CH3:36]C([N-]C(C)C)C.CCCCCCC.O1CCCC1.C(C1C=CC=CC=1)C.C[Si](C=[N+]=[N-])(C)C>O1CCCC1.CO.C(OCC)C>[C:29]([O:28][CH:24]([C:15]1[N:14]([CH3:33])[C:13](=[O:34])[C:12]2[NH:8][CH:9]=[CH:10][C:11]=2[C:16]=1[C:17]1[CH:18]=[CH:19][C:20]([CH3:23])=[CH:21][CH:22]=1)[C:25]([O:27][CH3:36])=[O:26])([CH3:31])([CH3:32])[CH3:30]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

8

Edukt 4

HCID 167693Trimethylsilyldiazomethane2×HCID 2724682Lithium diisopropylamide2×HCID 22742125Tetrahydrofuran heptane ethylbenzolHCID 71538481HCID 71538481, Verbindung

Produkt 1

HCID 89462627methyl 2-(tert-butoxy)-2-(6-methyl-7-oxo-4-(p-tolyl)-6,7-dihydro-1H-pyrrolo[2,3-c]pyridin-5-yl)acetate

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 887MethanolLösungsmittelHCID 3283Diethyl EtherLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

An ice cold mixture of 2-(1-benzyl-6-methyl-7-oxo-4-(p-tolyl)-6,7-dihydro-1H-pyrrolo[2,3-c]pyridin-5-yl)-2-(tert-butoxy)acetic acid (64.0 mg, 0.140 mmol) in Tetrahydrofuran (THF) (2.0 mL) was treated with dropwise addition of LDA, 2M solution in heptane/THF/ethylbenzene (0.140 mL, 0.279 mmol) and then allowed to stir at 0° C. for 45 minutes. Additional LDA (70 uL) was added and then stirred an additional 10 minutes. The mixture was quenched by adding 1N HCl and acidified to pH 2. The mixture was extracted with ethyl acetate. The combined extracts were washed with brine, dried over sodium sulfate, filtered and concentrated to give the crude debenzylation product as an orange residue. An ice cold mixture of the crude debenzylation product in methanol (1.0 mL) and diethyl ether (1.0 mL) was treated with trimethylsilyl diazomethane, 2M solution in hexanes (0.140 mL, 0.279 mmol) and then stirred at ambient temperature for 10 minutes. Additional trimethylsilyl diazomethane, 2M solution in hexanes (0.140 mL, 0.279 mmol) was added, the mixture was stirred for 5 minutes, cooled to 0° C. and then quenched with AcOH. The mixture was concentrated and then purified on silica gel (0-10% DCM/MeOH) to give the slightly impure desired product as a yellow residue (39 mg, 73% yield) which was used in the subsequent step without further purification. LC/MS (m/z) ES+=383 (M+1).

Aufarbeitung

  1. stirringstirred an additional 10 minutes
  2. customThe mixture was quenched
  3. additionby adding 1N HCl
  4. extractionThe mixture was extracted with ethyl acetate
  5. washThe combined extracts were washed with brine
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customto give the crude debenzylation product as an orange residue
  10. stirringstirred at ambient temperature for 10 minutes
  11. stirringthe mixture was stirred for 5 minutes
  12. temperaturecooled to 0° C.
  13. customquenched with AcOH
  14. concentrationThe mixture was concentrated
  15. custompurified on silica gel (0-10% DCM/MeOH)

Quellen und Nachweise

ORD-Eintrag
ord-63d659ad023e477da4ca2936a9f968c8
Quelldatensatz
uspto-grants-2015_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09012642B2

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