1-Hydroxybenzotriazole → N-[(3aS*,4S*,6aR*)-2-benzyloctahydrocyclopenta[c]pyrrol-4-yl]-2,2-dicyclohexylacetamide

HRID 1092468

Reaktionsgleichung

Reaktionsgleichung von HRID 1092468
[CH2:1]([N:8]1[CH2:12][C@H:11]2[CH:13]([NH2:16])[CH2:14][CH2:15][C@H:10]2[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH:17]1([CH:23]([CH:27]2[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]2)[C:24](O)=[O:25])[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]1.ON1C2C=CC=CC=2N=N1.CC[N+](CCCN(C)C)=C=N>ClCCl>[CH2:1]([N:8]1[CH2:12][C@H:11]2[C@@H:13]([NH:16][C:24](=[O:25])[CH:23]([CH:17]3[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]3)[CH:27]3[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]3)[CH2:14][CH2:15][C@H:10]2[CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Komponenten

6

Edukt 4

HCID 757711-HydroxybenzotriazoleHCID 3661562Dicyclohexylacetic acidHCID 218833923-(Dimethylamino)propyl-ethyl-(iminomethylidene)azaniumHCID 68411161(3aS*,6aR*)-2-benzyloctahydrocyclopenta[c]pyrrol-4-amine

Produkt 1

HCID 54674167N-[(3aS*,4S*,6aR*)-2-benzyloctahydrocyclopenta[c]pyrrol-4-yl]-2,2-dicyclohexylacetamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

(3aS*,6aR*)-2-Benzyloctahydrocyclopenta[c]pyrrol-4-amine (500 mg, 2.311 mmol), 2,2-dicyclohexylacetic acid (570 mg, 2.54 mmol), and 1-hydroxybenzotriazole (389 mg, 2.54 mmol) were combined in dichloromethane (20 mL). The reaction was stirred at room temperature for 10 minutes, then N-(3-dimethylaminopropyl)-N-ethylcarbodiimide (0.449 mL, 2.54 mmol) was added dropwise. The reaction was stirred at room temperature for 20 hours, and then the reaction was quenched with 10 mL of water. The reaction was extracted with 2×20 mL of dichloromethane, the solvent was removed in vacuo, and the crude material was chromatographed over a silica gel cartridge (Analogix®, Burlington, Wis., RS-40) eluting with 30-50% ethyl acetate/hexanes to give the title compound: 1H NMR (500 MHz, pyridine-d5) δ ppm 7.60 (d, J=5.1, 1H), 7.45-7.38 (m, 4H), 7.35 (m, 1H), 4.49-4.41 (m, 1H), 3.57 (d, J=12.6, 1H), 3.37 (d, J=12.5, 1H), 2.76 (d, J=9.6, 1H), 2.69 (dd, J=7.9, 15.7, 1H), 2.50 (d, J=9.1, 1H), 2.48-2.41 (m, 1H), 2.28 (t, J=8.2, 1H), 2.15-2.08 (m, 1H), 1.99-1.06 (m, 26H), 1.04-0.92 (m, 1H); MS (ESI+) m/z 423 (M+H)+.

Aufarbeitung

  1. stirringThe reaction was stirred at room temperature for 20 hours
  2. customthe reaction was quenched with 10 mL of water
  3. extractionThe reaction was extracted with 2×20 mL of dichloromethane
  4. customthe solvent was removed in vacuo
  5. customthe crude material was chromatographed over a silica gel cartridge (Analogix®, Burlington, Wis., RS-40)
  6. washeluting with 30-50% ethyl acetate/hexanes

Quellen und Nachweise

ORD-Eintrag
ord-1524d09d48364c35b2fd2fecdad0652b
Quelldatensatz
uspto-grants-2012_03
Patentnummer
US08129417B2

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