cis-2-Benzylhexahydrocyclopenta[c]pyrrol-4(1H)-one → HCID 11629873, compound

HRID 2402739Notes

Reaction equation

HRID 2402739 reaction equation
[CH2:1]([N:8]1[CH2:12][C@@H:11]2[C:13](=O)[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.[CH3:17]C(C)([O-])C.[K+]>O1CCCC1.[Br-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH2:1]([N:8]1[CH2:12][C@@H:11]2[C:13](=[CH2:17])[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

Participants

5

Reactant 2

HCID 13463770cis-2-Benzylhexahydrocyclopenta[c]pyrrol-4(1H)-oneHCID 23665647Potassium tert-butoxide

Product 1

HCID 11629873HCID 11629873, compound

Reagents, catalysts & solvents 2

HCID 74505Methyltriphenyliphosphonium bromideCatalystHCID 8028TetrahydrofuranSolvent

Procedure

The title compound was prepared by combining (3aR,6aS)-2-benzylhexahydrocyclopenta[c]pyrrol-4(5H)-one (100 mg, 0.464 mmol) [prepared as described by Santora, V. J., et. al. Bioorganic & Medicinal Chemistry Letters 2008, 18(4), 1490-1494] in 2 mL of tetrahydrofuran with methyltriphenylphosphonium bromide (249 mg, 0.697 mmol) and potassium tert-butoxide (78 mg, 0.697 mmol). The reaction was stirred at room temperature overnight, concentrated, and the crude material was purified by silica gel chromatography using 1-100% ethyl acetate/hexanes to give the title compound: 1H NMR (400 MHz, pyridine-d5) δ ppm 7.47-7.41 (m, 2H), 7.40-7.33 (m, 2H), 7.31-7.25 (m, 1H), 4.93-4.89 (m, 1H), 4.80-4.76 (m, 1H), 3.55 (d, J=13.1, 1H), 3.47 (d, J=13.1, 1H), 2.96-2.87 (m, 1H), 2.63-2.41 (m, 5H), 2.33 (dd, J=8.9, 3.9, 1H), 2.17 (dddt, J=14.9, 7.4, 5.8, 1.6, 1H), 1.68 (ddd, J=16.0, 12.4, 8.1, 1H), 1.51-1.39 (m, 1H); MS (ESI+) m/z 227 (M+H)+.

Workup

  1. customThe title compound was prepared
  2. concentrationconcentrated
  3. customthe crude material was purified by silica gel chromatography

Sources & evidence

ORD record
ord-ede80b2309084dab8e711a453e795eb8
Source dataset
uspto-grants-2014_08
Patent number
US08796470B2

Reaction notes

Loading…