Potassium tert-butoxide → HCID 58598878, compound

HRID 1020334Notes

Reaction equation

HRID 1020334 reaction equation
[CH3:1][C:2](C)([O-])C.[K+].C([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)C1C=CC=CC=1>[Br-].C([P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)C.CCOCC>[CH3:27][O:26][C:20]1[CH:21]=[CH:22][C:23]2[CH:24]([CH2:1][CH3:2])[CH:16]3[CH2:15][NH:14][CH2:28][CH:17]3[C:18]=2[CH:19]=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 58598878HCID 58598878, compound

Reagents, catalysts & solvents 2

HCID 73727Phosphonium, ethyltriphenyl-, bromide (1:1)CatalystHCID 3283Diethyl EtherSolvent

Procedure

Ethyltriphenylphosphonium bromide (0.6 g, 1.6 mmol) and potassium tert-butoxide (0.18 g, 1.6 mmol) were added to a solution of 2-benzyl-5-methoxy-2,3,3a,8a-tetrahydro-1H-2-aza-cyclopenta[a]inden-8-one (from Example 1, Step C) (0.32 g, 1.1 mmol) in anhydrous ether (2.2 mL). The reaction mixture was stirred for 1 hour at room temperature then filtered through celite. The celite was washed with ether (10 mL), and the filtrate was concentrated. The crude product was purified by column chromatography (SiO2) using a 0-35% EtOAc-hexanes gradient to afford the subtitle compound in quantitative yield. MS calculated for C21H23NO+H: 306, observed: 306.

Workup

  1. filtrationthen filtered through celite
  2. washThe celite was washed with ether (10 mL)
  3. concentrationthe filtrate was concentrated
  4. customThe crude product was purified by column chromatography (SiO2)

Sources & evidence

ORD record
ord-e7472ef5927249c9888ba2eb559c454d
Source dataset
uspto-grants-2014_05
Patent number
US08716324B2

Reaction notes

Loading…