(-) (2aR,4S)-6-(2-oxazolyl)-4-(di-n-propylamino)-1,2,2a,3,4,5-hexahydrobenz[cd]indole → (-) (4R)-6-(2-oxazolyl)-4-(di-n-propylamino)-1,3,4,5-tetrahydrobenz[cd]indole

HRID 2379752Notes

Reaction equation

HRID 2379752 reaction equation
[O:1]1[CH:5]=[CH:4][N:3]=[C:2]1[C:6]1[CH:14]=[CH:13][C:12]2[NH:11][CH2:10][C@@H:9]3[CH2:15][C@H:16]([N:18]([CH2:22][CH2:23][CH3:24])[CH2:19][CH2:20][CH3:21])[CH2:17][C:7]=1[C:8]=23>C(Cl)Cl.O=[Mn]=O>[O:1]1[CH:5]=[CH:4][N:3]=[C:2]1[C:6]1[CH:14]=[CH:13][C:12]2[NH:11][CH:10]=[C:9]3[CH2:15][C@H:16]([N:18]([CH2:22][CH2:23][CH3:24])[CH2:19][CH2:20][CH3:21])[CH2:17][C:7]=1[C:8]=23

Participants

4

Reactant 1

HCID 18654736(-) (2aR,4S)-6-(2-oxazolyl)-4-(di-n-propylamino)-1,2,2a,3,4,5-hexahydrobenz[cd]indole

Product 1

HCID 10663705(-) (4R)-6-(2-oxazolyl)-4-(di-n-propylamino)-1,3,4,5-tetrahydrobenz[cd]indoleYield 37.1%

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalystHCID 6344DichloromethaneSolvent

Procedure

A solution of 0.65 g (2.0 mmol) of (-) (2aR,4S)-6-(2-oxazolyl)-4-(di-n-propylamino)-1,2,2a,3,4,5-hexahydrobenz[cd]indole in 30 ml of CH2Cl2 was sonicated (50-55 KHz) in the presence of 2.5 g of MnO2 for 5 hours. The oxidant was removed by filtration through celite. The crude product obtained after filtering and removing the solvent was chromatographed over 15 g of silica gel using 1:9 EtOAc/toluene, then crystallized from isooctane to provide 0.24 g of title compound.

Workup

  1. customThe oxidant was removed by filtration through celite
  2. customThe crude product obtained
  3. filtrationafter filtering
  4. customremoving the solvent
  5. customwas chromatographed over 15 g of silica gel using 1:9 EtOAc/toluene
  6. customcrystallized from isooctane

Sources & evidence

ORD record
ord-5639126d5d0745538d8915b022c1f06c
Source dataset
uspto-grants-1994_11
Patent number
US05364856

Reaction notes

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