Boron Trichloride → HCID 67424379, compound

HRID 1392998Notes

Reaction equation

HRID 1392998 reaction equation
C[O:2][C:3]1[CH:19]=[CH:18][C:6]2[CH:7]3[C:14]4([CH2:15][CH2:16][C:5]=2[CH:4]=1)[CH:10]([CH2:11][N:12]([CH3:17])[CH2:13]4)[CH2:9][CH2:8]3.B(Cl)(Cl)Cl>[I-].C([N+](CCCC)(CCCC)CCCC)CCC.C(Cl)Cl>[CH3:17][N:12]1[CH2:13][C:14]23[CH:7]([CH2:8][CH2:9][CH:10]2[CH2:11]1)[C:6]1[CH:18]=[CH:19][C:3]([OH:2])=[CH:4][C:5]=1[CH2:16][CH2:15]3

Participants

5

Reactant 2

HCID 25135Boron TrichlorideHCID 56660575HCID 56660575, compound

Product 1

HCID 67424379HCID 67424379, compoundYield 31.8%

Reagents, catalysts & solvents 2

HCID 67553Tetrabutylammonium IodideCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
-78 °C

Procedure

2-Methoxy-8-methyl-5,6,6a,7,8,9,10,11-octahydro-4bH-benzo[4,5]indeno[1,7a-c]pyrrole (Example 1B) (190.0 mg, 0.74 mmol) and tetrabutylammonium iodide (300 mg, 0.81 mmol) were dissolved in CH2Cl2 (20 mL) and cooled to −78° C. BCl3 (1.85 mL, 1M in CH2Cl2) was added dropwise. The mixture was stirred at 0° C. for 5 hrs. It was then quenched with aq. satd. NaHCO3, extracted with CH2Cl2 (15 mL×4). The combined organic layers were dried over sodium sulfate, filtered and concentrated in vacuo. The residue was purified by column chromatography on silica gel using 5% methanol in dichloromethane, providing 57.1 mg (31.8%) of the title compound 1C.

Workup

  1. customIt was then quenched with aq. satd
  2. extractionNaHCO3, extracted with CH2Cl2 (15 mL×4)
  3. dry with materialThe combined organic layers were dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by column chromatography on silica gel using 5% methanol in dichloromethane

Sources & evidence

ORD record
ord-38dc83eaf4064da38da238cfcbe23777
Source dataset
uspto-grants-2008_03
Patent number
US07345034B2

Reaction notes

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