rac-cis-3-(2-cyclohexylethyl)-2,3,3a,4,5,9b-hexahydro-6-methoxy-1H-benz[e]indole → (+)-cis-3-(2-cyclohexylethyl)-2,3,3a,4,5,9b-hexahydro-1H-benzo[e]indol-6-ol

HRID 1109172Notes

Reaction equation

HRID 1109172 reaction equation
[CH:1]1([CH2:7][CH2:8][N:9]2[C@@H:17]3[C@@H:12]([C:13]4[CH:21]=[CH:20][CH:19]=[C:18]([O:22]C)[C:14]=4[CH2:15][CH2:16]3)[CH2:11][CH2:10]2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1>Br>[CH:1]1([CH2:7][CH2:8][N:9]2[C@@H:17]3[C@@H:12]([C:13]4[CH:21]=[CH:20][CH:19]=[C:18]([OH:22])[C:14]=4[CH2:15][CH2:16]3)[CH2:11][CH2:10]2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

3

Reactant 1

HCID 131718424rac-cis-3-(2-cyclohexylethyl)-2,3,3a,4,5,9b-hexahydro-6-methoxy-1H-benz[e]indole

Product 1

HCID 86747896(+)-cis-3-(2-cyclohexylethyl)-2,3,3a,4,5,9b-hexahydro-1H-benzo[e]indol-6-olYield 68.8%

Reagents, catalysts & solvents 1

HCID 260Hydrogen BromideSolvent

Procedure

16.1 g (0.05 mol) of rac-cis-3-(2-cyclohexylethyl)-2,3,3a,4,5,9b-hexahydro-6-methoxy-1H-benz[e]indole were boiled at 120° for 3 hours with 270 ml of 48 percent aqueous hydrobromic acid. After distilling off the hydrobromic acid in a vacuum the residue was dissolved in methylene chloride/water. After extraction with methylene chloride at pH 8 the solvent was distilled off in a vacuum. After chromatography over silica gel (methylene chloridemethanol 10:1) there were obtained 10.3 g (67%) of rac-cis-3-(2-cyclohexylethyl)-2,3,3a,4,5,9b-hexahydro-1H-benzo[e]indol-6-ol as a beige oil.

Workup

  1. customfor 3 hours
  2. distillationAfter distilling off the hydrobromic acid in a vacuum the residue
  3. dissolutionwas dissolved in methylene chloride/water
  4. extractionAfter extraction with methylene chloride at pH 8 the solvent
  5. distillationwas distilled off in a vacuum

Sources & evidence

ORD record
ord-e46e1a38976d40d18dc9c2e4fa48ee2a
Source dataset
uspto-grants-1994_06
Patent number
US05318967

Reaction notes

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