StartseiteMCPWorkbenchSkills
StartseiteWorkbenchBenachrichtigungenMein Bereich
llms.txt · MCP-AnleitungDatenschutz · Nutzungsbedingungen · Supportv1.8.0
  1. Startseite
  2. /Reaktion

Benzene → (1S,2S) 2-Ethyl-1-(2trimethylsilanylethoxycarbonylamino)cyclopropane-carboxylic acid tert-butyl ester

HRID 339154
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 339154
C(OC([C@@]1(N[C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])C[C@H]1C1CC1)=O)C.CC[N:22]([CH2:25][CH3:26])[CH2:23]C.C1C=CC(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:34])=CC=1.[CH3:44][Si:45]([CH3:50])([CH3:49])[CH2:46][CH2:47][OH:48].[CH:51]1[CH:56]=CC=C[CH:52]=1>>[C:16]([O:15][C:13]([C@:25]1([NH:22][C:23]([O:48][CH2:47][CH2:46][Si:45]([CH3:50])([CH3:49])[CH3:44])=[O:34])[CH2:26][C@@H:52]1[CH2:51][CH3:56])=[O:14])([CH3:17])([CH3:18])[CH3:19]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 5

HCID 241BenzeneHCID 8471TriethylamineHCID 180132-(Trimethylsilyl)ethanolHCID 199401P,P-Diphenylphosphinic azideHCID 59990838(1R,2S)-ethyl 1-(tert-butoxycarbonylamino)-2-cyclopropylcyclopropanecarboxylate

Produkt 1

HCID 86601847
(1S,2S) 2-Ethyl-1-(2trimethylsilanylethoxycarbonylamino)cyclopropane-carboxylic acid tert-butyl ester
Ausbeute 52 %

Versuchsvorschrift

To a suspension, of the product of Step 2 (10 g, 46.8 mmol) and 3 g of freshly activated 4A molecular sieves in dry benzene (160 mL), was added Et3N (7.50 mL, 53.8 mmol) and DPPA (11 mL, 10.21 mmol). The reaction mixture was refluxed for 3.5 h, 2-trimethylsilyl-ethanol (13.5 mL, 94.2 mmol) was then added, and the reaction mixture was refluxed overnite. The reaction mixture was filtered, diluted with Et2O, washed with a 10% aqueous citric acid solution, water, saturated aqueous NaHCO3, water (2×), brine (2×), dried (MgSO4) and concentrated in vacuo. The residue was suspended with 10 g of Aldrich polyisocyanate scavenger resin in 120 mL of CH2Cl2, stirred at rt overnite and filtered to afford the titled product (8 g, 24.3 mmol; 52%) as a pale yellow oil: 1H NMR (CDCl3) δ 0.03 (s, 9H), 0.97 (m, 5H), 1.20 (bm, 1H), 1.45 (s, 9H), 1.40-1.70 (m, 4H), 4.16 (m, 2H), 5.30 (bs, 1H).

Aufarbeitung

  1. temperatureThe reaction mixture was refluxed for 3.5 h
  2. temperaturethe reaction mixture was refluxed overnite
  3. filtrationThe reaction mixture was filtered
  4. additiondiluted with Et2O
  5. washwashed with a 10% aqueous citric acid solution, water, saturated aqueous NaHCO3, water (2×), brine (2×)
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated in vacuo
  8. filtrationfiltered

Quellen und Nachweise

ORD-Eintrag
ord-a5b5b80c7fc6482aa8367aea65895be5
Quelldatensatz
uspto-grants-2014_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08889871B2

Notizen zur Reaktion

Wird geladen…

Auf dieser SeiteKomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion