Trifluoroacetic acid → (3aR,5R,6aR)-Methyl 2-benzyl-5-((tert-butoxycarbonyl)amino)octahydro-cyclopenta[c]pyrrole-3a-carboxylate

HRID 571350Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 571350
[CH3:1][O:2][C:3]([C:5]1[CH2:9][C@H:8]([NH:10][C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:7][CH:6]=1)=[O:4].CO[CH2:20][N:21]([CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)[CH2:22][Si](C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH2:27]([N:21]1[CH2:22][C@@:5]2([C:3]([O:2][CH3:1])=[O:4])[CH2:9][C@H:8]([NH:10][C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:7][C@H:6]2[CH2:20]1)[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1

Komponenten

5

Edukt 3

HCID 6422Trifluoroacetic acidHCID 353442Benzyl(methoxymethyl)((trimethylsilyl)methyl)amineHCID 10586185methyl (4R)-4-{[(tert-butoxy)carbonyl]amino}cyclopent-1-ene-1-carboxylate

Produkt 1

HCID 86708893(3aR,5R,6aR)-Methyl 2-benzyl-5-((tert-butoxycarbonyl)amino)octahydro-cyclopenta[c]pyrrole-3a-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

To a solution of the product from Step B (5.51 g, 20 mmol) and N-(methoxymethyl)-N-(trimethylsilylmethyl)benzylamine (6.4 mL, 24 mmol, Aldrich) in DCM (40 mL) was added 1M TFA in DCM (2.4 mL, 2.4 mmol) slowly. The resulting mixture was stirred at rt overnight and quenched by the addition of saturated aqueous NaHCO3 solution. The organic phase was washed with brine, dried over Na2SO4. Evaporation and purification by column chromatography (eluent: 10% EtOAc in hexanes to 20%) gave the desired isomer as a colorless gel. 1H-NMR (400 MHz, CDCl3) of the desired isomer: δ 1.38 (s, 9H), 1.66-1.86 (m, 2H), 1.86-1.96 (m, 1H), 1.96-2.08 (m, 1H), 2.29-2.63 (m, 3H), 2.71-2.93 (m, 2H), 3.43-3.56 (m, 2H), 3.58-3.74 (s, 3H), 4.08-4.29 (m, 1H), 4.78 (d, J=6.6 Hz, 1H), 7.11-7.31 (m, 5H). LC/MS: C24H28N2O4: m/z 375.2 (M+H).

Aufarbeitung

  1. customquenched by the addition of saturated aqueous NaHCO3 solution
  2. washThe organic phase was washed with brine
  3. dry with materialdried over Na2SO4
  4. customEvaporation and purification by column chromatography (eluent: 10% EtOAc in hexanes to 20%)
  5. customgave the desired isomer as a colorless gel

Quellen und Nachweise

ORD-Eintrag
ord-d3fa2e254a6c46fe8a5b9f317cd57b4a
Quelldatensatz
uspto-grants-2015_05
Patentnummer
US09024017B2

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