Triethylamine → Methyl (R)-3-((tert-butoxycarbonyl)amino)-2,3-dihydro-1H-indene-5-carboxylate

HRID 1193250Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1193250
Br[C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][CH2:7][C@H:8]2[NH:11][C:12](=[O:18])[O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[CH:4][CH:3]=1.C1C=CC(P(C2C=CC=CC=2)CCCP(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C(N(CC)CC)C>CO.CS(C)=O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[C:14]([O:13][C:12]([NH:11][C@H:8]1[C:9]2[C:5](=[CH:4][CH:3]=[C:2]([C:12]([O:13][CH3:14])=[O:18])[CH:10]=2)[CH2:6][CH2:7]1)=[O:18])([CH3:17])([CH3:16])[CH3:15]

Komponenten

7

Edukt 3

HCID 8471TriethylamineHCID 812191,3-Bis(diphenylphosphino)propaneHCID 59505686(R)-(6-Bromo-indan-1-yl)-carbamic acid tert-butyl ester

Produkt 1

HCID 59505324Methyl (R)-3-((tert-butoxycarbonyl)amino)-2,3-dihydro-1H-indene-5-carboxylateAusbeute 76 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 167845palladium(II) acetateKatalysatorHCID 679Dimethyl SulfoxideLösungsmittelHCID 887MethanolLösungsmittel

Versuchsvorschrift

(R)-tert-Butyl 6-bromo-2,3-dihydro-1H-inden-1-ylcarbamate (15.0 g, 48.07 mmol, 1 eq) was dissolved in a mixture of methanol (200 ml) and DMSO (30 ml) and degassed for 30 min with argon, and palladium acetate (0.53 g, 2.40 mmol, 0.05 eq), 1,3-bis(diphenylphosphine)-propane (0.99 g, 2.40 mmol, 0.05 eq) and triethylamine (20 ml, 144.21 mmol, 3.0 eq) were added. In an autoclave, the reaction was sealed for 16 h at 75° C. at CO pressure (80 psi). Then the reaction mixture was dried under reduced pressure, and the residue was taken up in water (150 ml) and extracted with ethyl acetate (2×300 ml). The combined organic phases were washed with sat. NaCl solution (100 ml), dried over sodium sulfate and concentrated under reduced pressure. The crude product was purified by column chromatography (silica gel, 5% ethyl acetate in hexane) to give the desired product in the form of a white solid. Yield: 76% (10.6 g, 36.43 mmol).

Aufarbeitung

  1. additionwere added
  2. customIn an autoclave, the reaction was sealed for 16 h at 75° C. at CO pressure (80 psi)
  3. customThen the reaction mixture was dried under reduced pressure
  4. extractionextracted with ethyl acetate (2×300 ml)
  5. washThe combined organic phases were washed with sat. NaCl solution (100 ml)
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe crude product was purified by column chromatography (silica gel, 5% ethyl acetate in hexane)

Quellen und Nachweise

ORD-Eintrag
ord-c2c42bc7818d4003a2a84fa7ee01c3cf
Quelldatensatz
uspto-grants-2014_03
Patentnummer
US08680159B2

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