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Sodium Hydroxide → 5-Chloro-6-methyl-3,3a,7,7a-tetrahydro-1H-4-thia-2-aza-cyclopenta[alpha]pentalene-2-carboxylic acid ethyl ester

HRID 30244
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 30244
[Cl-].[Al+3].[Cl-].[Cl-].C(NB)(C)(C)C.[CH2:11]([O:13][C:14]([N:16]1[CH2:23][CH:22]2[CH:18]([CH2:19][C:20]3[C:26]([CH2:27]O)=[C:25]([Cl:29])[S:24][C:21]=32)[CH2:17]1)=[O:15])[CH3:12].[OH-].[Na+]>C(Cl)Cl>[CH2:11]([O:13][C:14]([N:16]1[CH2:23][CH:22]2[CH:18]([CH2:19][C:20]3[C:26]([CH3:27])=[C:25]([Cl:29])[S:24][C:21]=32)[CH2:17]1)=[O:15])[CH3:12]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 14798Sodium HydroxideHCID 3639180N-boranyl-2-methylpropan-2-amineHCID 6451240Aluminum(III) ChlorideHCID 1317270275-Chloro-6-hydroxymethyl-3,3a,7,7a-tetrahydro-1H-4-thia-2-aza-cyclopenta[alpha]pentalene-2-carboxylic acid ethyl ester

Produkt 1

HCID 1317270265-Chloro-6-methyl-3,3a,7,7a-tetrahydro-1H-4-thia-2-aza-cyclopenta[alpha]pentalene-2-carboxylic acid ethyl ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

Aluminum chloride (131.7 mg, 0.990 mmol) was added to a round bottom flask, cooled to 0° C. and diluted with anhydrous CH2Cl2 (3.3 ml). Next, tert-butylaminoborane (172 mg, 1.98 mmol) was added and the contents were stirred for 30 minutes. A solution of 5-Chloro-6-hydroxymethyl-3,3a,7,7a-tetrahydro-1H-4-thia-2-aza-cyclopenta[α]pentalene-2-carboxylic acid ethyl ester (99.7 mg, 0.33 mmol) in CH2Cl2 (330 μl) was added to the AlC13/t-butylaminoborane complex. The reaction mixture slowly warmed to room temperature and stirred for 16 hours. Next, the contents were carefully poured into 15% NaOH and extracted with CH2Cl2 (2×50 ml). The organic layer was dried (MgSO4), solvent evaporated in vacuo, and the residue purified by preparative TLC (hexanes:EtOAc-7:3) to give the subtitle compound. MS calculated for C13H16ClNO2S+H 286, observed 286.

Aufarbeitung

  1. temperatureThe reaction mixture slowly warmed to room temperature
  2. stirringstirred for 16 hours
  3. extractionextracted with CH2Cl2 (2×50 ml)
  4. dry with materialThe organic layer was dried (MgSO4), solvent
  5. customevaporated in vacuo
  6. customthe residue purified by preparative TLC (hexanes:EtOAc-7:3)

Quellen und Nachweise

ORD-Eintrag
ord-a640b5da28a545da9b021138c0f7e967
Quelldatensatz
uspto-grants-2008_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07423056B2

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