Sodium Hydroxide → rac-N-[5-(cis-1,2,3a,4,5,9b-hexahydro-6-hydroxy-3H-benzo[e]indol-3-yl)pentyl]phthalimide

HRID 1109233Notes

Reaction equation

HRID 1109233 reaction equation
C[O:2][C:3]1[C:15]2[CH2:14][CH2:13][C@H:12]3[C@H:8]([CH2:9][CH2:10][N:11]3[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][N:21]3[C:25](=[O:26])[C:24]4=[CH:27][CH:28]=[CH:29][CH:30]=[C:23]4[C:22]3=[O:31])[C:7]=2[CH:6]=[CH:5][CH:4]=1.B(Br)(Br)Br.[OH-].[Na+].C(=O)([O-])O.[Na+]>C(Cl)Cl.O>[OH:2][C:3]1[C:15]2[CH2:14][CH2:13][C@H:12]3[C@H:8]([CH2:9][CH2:10][N:11]3[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][N:21]3[C:22](=[O:31])[C:23]4=[CH:30][CH:29]=[CH:28][CH:27]=[C:24]4[C:25]3=[O:26])[C:7]=2[CH:6]=[CH:5][CH:4]=1

Participants

7

Reactant 4

HCID 14798Sodium HydroxideHCID 25134Boron tribromideHCID 516892Sodium BicarbonateHCID 131718501rac-N-[5-(cis-1,2,3a, 4,5,9b-hexahydro-6-methoxy-3H-benzo[e]indol-3-yl)pentyl]phthalimide

Product 1

HCID 131718502rac-N-[5-(cis-1,2,3a,4,5,9b-hexahydro-6-hydroxy-3H-benzo[e]indol-3-yl)pentyl]phthalimideYield 21.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 15.0 g (0.036 mol) of rac-N-[5-(cis-1,2,3a,4,5,9b-hexahydro-6-methoxy-3H-benzo[e]indol-3-yl)pentyl]phthalimide in 120 ml of methylene chloride was treated dropwise with a solution of 17.3 ml (0.179 mol) of boron tribromide in 60 ml of methylene chloride, whereupon the mixture was stirred at 0° for 2 hours. A solution of 20.4 g (0.51 mol) of sodium hydroxide in 70 ml of water was added dropwise while cooling with an ice bath. The mixture was poured into water, whereupon aqueous sodium hydrogen carbonate solution was added until a pH of 8 had been reached. The mixture was extracted with methylene chloride, the extracts were dried over sodium sulphate and the solvent was distilled off in a vacuum. Chromatography over silica gel with ethyl acetate yielded 3.1 g (21%) of rac-N-[5-(cis-1,2,3a,4,5,9b-hexahydro-6-hydroxy-3H-benzo[e]indol-3-yl)pentyl]phthalimide as a brown oil. A small sample was converted with ethanolic HCl into the hydrochloride, m.p. 246°-248°.

Workup

  1. temperaturewhile cooling with an ice bath
  2. additionwas added until a pH of 8
  3. extractionThe mixture was extracted with methylene chloride
  4. dry with materialthe extracts were dried over sodium sulphate
  5. distillationthe solvent was distilled off in a vacuum

Sources & evidence

ORD record
ord-3b5e161333f44d6184012b01c2b5d0f3
Source dataset
uspto-grants-1994_06
Patent number
US05318967

Reaction notes

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