Potassium tert-butoxide → 2-Benzyl-5-methoxy-8-methylene-1,2,3,3a,8,8a-hexahydroindeno[1,2-c]pyrrole

HRID 546281Notes

Reaction equation

HRID 546281 reaction equation
[CH3:1]C(C)([O-])C.[K+].[CH2:7]([N:14]1[CH2:28][CH:17]2[C:18]3[CH:19]=[C:20]([O:26][CH3:27])[CH:21]=[CH:22][C:23]=3[C:24](=O)[CH:16]2[CH2:15]1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1>[Br-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.CCOCC>[CH2:7]([N:14]1[CH2:15][CH:16]2[C:24](=[CH2:1])[C:23]3[CH:22]=[CH:21][C:20]([O:26][CH3:27])=[CH:19][C:18]=3[CH:17]2[CH2:28]1)[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Participants

5

Reactant 2

HCID 23665647Potassium tert-butoxideHCID 672034582-Benzyl-5-methoxy-2,3,3a,8a-tetrahydro-1H-2-aza-cyclopenta[a]inden-8-one

Product 1

HCID 672038462-Benzyl-5-methoxy-8-methylene-1,2,3,3a,8,8a-hexahydroindeno[1,2-c]pyrrole

Reagents, catalysts & solvents 2

HCID 74505Methyltriphenyliphosphonium bromideCatalystHCID 3283Diethyl EtherSolvent

Procedure

Methyltriphenylphosphonium bromide (18.1 g, 50.7 mmol) and potassium tert-butoxide (5.7 g, 50.7) were added to a solution of 2-benzyl-5-methoxy-2,3,3a,8a-tetrahydro-1H-2-aza-cyclopenta[a]inden-8-one (9.9 g, 33.8 mmol) in anhydrous ether (68 mL). The reaction mixture was stirred for 1 hour at room temperature then filtered through celite. The celite was washed with ether (200 mL), and the filtrate was concentrated. The crude product was purified by column chromatography (SiO2) using a 0-35% ethyl acetate-hexanes gradient to afford 8.1 g (82%-two steps) of the subtitle compound. MS calculated for C20H21NO+H: 292, observed: 292.

Workup

  1. filtrationthen filtered through celite
  2. washThe celite was washed with ether (200 mL)
  3. concentrationthe filtrate was concentrated
  4. customThe crude product was purified by column chromatography (SiO2)

Sources & evidence

ORD record
ord-289deff3f4f54a26b4cfbc8e29841b12
Source dataset
uspto-grants-2011_05
Patent number
US07935830B2

Reaction notes

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