HCID 57475162, compound → HCID 57475061, compound

HRID 1095564Notes

Reaction equation

HRID 1095564 reaction equation
[CH3:1][N:2]([CH3:29])[C:3]1([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH2:8][CH2:7][C:6]([C:9]2[NH:10][C:11]3[C:16]([C:17]=2[CH2:18][C:19]([O:21][CH3:22])=[O:20])=[CH:15][CH:14]=[CH:13][CH:12]=3)=[CH:5][CH2:4]1>Br.CCO>[CH3:29][N:2]([CH3:1])[C:3]1([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH2:8][CH2:7][CH:6]([C:9]2[NH:10][C:11]3[C:16]([C:17]=2[CH2:18][C:19]([O:21][CH3:22])=[O:20])=[CH:15][CH:14]=[CH:13][CH:12]=3)[CH2:5][CH2:4]1

Participants

4

Reactant 1

HCID 57475162HCID 57475162, compound

Product 1

HCID 57475061HCID 57475061, compound

Reagents, catalysts & solvents 2

HCID 260Hydrogen BromideSolventHCID 702EthanolSolvent

Procedure

(±)-Methyl 2-(2-(4-(dimethylamino)-4-phenylcyclohex-1-enyl)-1H-indol-3-yl)acetate (936 mg, 2.4 mmol) was dissolved in HBr/glacial acetic acid (33% HBr, 30 ml). Sn powder (2.88 g, 24 mmol) was then added to the mixture in portions at RT in the course of 1 h. When the addition had ended, the reaction mixture was stirred at RT for a further 16 h.—For working up, the mixture was diluted with EtOH (10 ml) and concentrated to dryness on a rotary evaporator. The residue which remained was rendered basic by addition of 2 N NaOH (100 ml). The aqueous mixture obtained was extracted with methylene chloride (4×40 ml). The combined organic phases were dried over Na2SO4 and then concentrated. The crude product obtained (900 mg) was purified by column chromatography [silica gel 60 (100 g); MeOH (1,000 ml)] Methyl 2-(2-(4-(dimethylamino)-4-phenylcyclohexyl)-1H-indol-3-yl)acetate (less polar diastereomer) was obtained in a yield of 290 mg (31%), and the polar diastereomer was obtained in a yield of 200 mg (21%). Both products were colourless oils.

Workup

  1. additionWhen the addition
  2. concentrationconcentrated to dryness on a rotary evaporator
  3. additionThe residue which remained was rendered basic by addition of 2 N NaOH (100 ml)
  4. customThe aqueous mixture obtained
  5. extractionwas extracted with methylene chloride (4×40 ml)
  6. dry with materialThe combined organic phases were dried over Na2SO4
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-96617cc4d0254a72b9d0e2a619d03417
Source dataset
uspto-grants-2012_03
Patent number
US08138187B2

Reaction notes

Loading…