Tetrahydrofuran → 5-Methoxy-8-methyl-1,2,3,3a,8,8a-hexahydroindeno[1,2-c]pyrrole

HRID 1020299Notes

Reaction equation

HRID 1020299 reaction equation
C1CCN2[C:4](=[N:5][CH2:6]CC2)CC1.[CH3:12][O:13][C:14]1[CH:15]=[C:16]2[C:20](=[CH:21][CH:22]=1)[C:19](=O)[CH2:18][CH:17]2Br.[CH2:25]1COCC1>>[CH3:12][O:13][C:14]1[CH:22]=[CH:21][C:20]2[CH:19]([CH3:25])[CH:18]3[CH2:6][NH:5][CH2:4][CH:17]3[C:16]=2[CH:15]=1

Participants

4

Reactant 3

HCID 8028TetrahydrofuranHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 232506513-Bromo-5-methoxy-2,3-dihydro-1H-inden-1-one

Product 1

HCID 115429805-Methoxy-8-methyl-1,2,3,3a,8,8a-hexahydroindeno[1,2-c]pyrrole

Conditions

Temperature
-10 °C

Procedure

DBU (9.2 mL, 61.7 mmol) was added to a solution of 5-methoxy-3-bromo-1-indanone (14.8 g, 61.7 mmol) in THF (100 mL) at −10° C. dropwise over 10 minutes. The resulting solution was stirred at −10° C. for 20 minutes, quenched via addition of saturated aqueous NH4Cl (100 mL), and extracted with EtOAc (3×100 mL). The combined organic extracts were washed with brine (100 mL), dried over MgSO4, and concentrated. The crude product was purified by column chromatography (SiO2) using a 0-35% ethyl acetate-hexanes gradient to afford 5.4 g (55%—two steps) of the subtitle compound. 1H NMR (CDCl3 300 MHz) δ 7.42 (d, 1H), 7.38 (d, 1H), 6.62 (s, 1H), 6.60 (d, 1H), 5.89 (d, 1H), 3.85 (s, 3H) ppm. MS calculated for C10H8O2+H: 161, observed: 161.

Workup

  1. customquenched via addition of saturated aqueous NH4Cl (100 mL)
  2. extractionextracted with EtOAc (3×100 mL)
  3. washThe combined organic extracts were washed with brine (100 mL)
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated
  6. customThe crude product was purified by column chromatography (SiO2)

Sources & evidence

ORD record
ord-b78b1b9e884c46bf92893025a09758fb
Source dataset
uspto-grants-2014_05
Patent number
US08716324B2

Reaction notes

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