Acetic Acid → (3aR*,4S*,6aS*)-N-benzyl-2-(3-methyl-2-phenylbutanoyl)octahydrocyclopenta[c]pyrrol-4-amine

HRID 1092564Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1092564
Cl.[NH2:2][C@@H:3]1[C@@H:10]2[C@@H:6]([CH2:7][N:8]([C:11](=[O:22])[CH:12]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[CH:13]([CH3:15])[CH3:14])[CH2:9]2)[CH2:5][CH2:4]1.[CH:23](=O)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.C(O)(=O)C.C([BH3-])#N>ClCCl>[CH2:23]([NH:2][C@@H:3]1[C@@H:10]2[C@@H:6]([CH2:7][N:8]([C:11](=[O:22])[CH:12]([C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=3)[CH:13]([CH3:15])[CH3:14])[CH2:9]2)[CH2:5][CH2:4]1)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Komponenten

6

Edukt 4

HCID 176Acetic AcidHCID 240BenzaldehydeHCID 498716Cyano-borohydrideHCID 665909011-((3aR,4S,6aS)-4-aminohexahydrocyclopenta[c]pyrrol-2(1H)-yl)-3-methyl-2-phenylbutan-1-one hydrochloric acid salt

Produkt 1

HCID 68413117(3aR*,4S*,6aS*)-N-benzyl-2-(3-methyl-2-phenylbutanoyl)octahydrocyclopenta[c]pyrrol-4-amine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

1-((3aR,4S,6aS)-4-aminohexahydrocyclopenta[c]pyrrol-2(1H)-yl)-3-methyl-2-phenylbutan-1-one hydrochloric acid salt (49 mg, 0.152 mmol) and benzaldehyde (0.023 mL, 0.228 mmol) were combined in dichloromethane (1.5 mL). Acetic acid (1.5 mL) was added. The reaction was stirred at room temperature for 30 minutes, then PS-cyanoborohydride (64.9 mg, 0.152 mmol) was added. After 72 hours, 1 cms of the reaction showed no more starting material. The reaction mixture was filtered, and the solvent was removed under a stream of nitrogen. The crude material was purified using a silica gel cartridge (Analogix®, Burlington, Wis., RS-4) eluting with 1-10% methanol (2 N ammonia)/dichloromethane to give the title compound: 1H NMR (500 MHz, pyridine-d5) δ ppm 7.69-7.60 (m, 2H), 7.54-7.44 (m, 2H), 7.44-7.34 (m, 5H), 7.29 (tdd, J=4.8, 7.8, 13.0, 2H), 3.90-3.36 (m, 4H), 3.29 (dd, J=3.8, 10.6, 0.5H), 2.99 (dd, J=5.7, 11.4, 0.5H), 2.93 (dd, J=6.0, 11.3, 0.5H), 2.75-2.63 (m, 1H), 2.59-2.48 (m, 1H), 2.46-2.31 (m, 1H), 2.25 (dt, J=4.1, 8.7, 0.5H), 1.97 (dt, J=9.3, 11.6, 1H), 1.93-1.85 (m, 0.5H), 1.84-1.74 (m, 1H), 1.65-1.55 (m, 0.5H), 1.51-1.35 (m, 1H), 1.33-1.21 (m, 1H), 1.18-1.10 (m, 3H), 1.01 (td, J=7.7, 13.1, 0.5H), 0.87 (dt, J=6.6, 12.9, 0.5H), 0.75 (t, J=7.2, 3H); MS (ESI+) m/z 377 (M+H)+.

Aufarbeitung

  1. waitAfter 72 hours
  2. filtrationThe reaction mixture was filtered
  3. customthe solvent was removed under a stream of nitrogen
  4. customThe crude material was purified
  5. washeluting with 1-10% methanol (2 N ammonia)/dichloromethane

Quellen und Nachweise

ORD-Eintrag
ord-8288927b47cd4c649ab4f1ca49eb06da
Quelldatensatz
uspto-grants-2012_03
Patentnummer
US08129417B2

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