Benzene → HCID 20353269, compound

HRID 372097Notes

Reaction equation

HRID 372097 reaction equation
BrBr.Br[C:4]12[C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=3[CH:11]3[CH:18](Br)[C:8]1([C:9]1[CH:23]=[CH:22][CH:21]=[CH:20][C:10]=13)[CH2:7][N:6]([CH2:24][CH:25]1[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]1)[C:5]2=[O:31].C([SnH](CCCC)CCCC)CCC.C1C=CC=CC=1>C(Cl)Cl>[CH:25]1([CH2:24][N:6]2[CH2:7][C:8]34[CH2:18][CH:11]([C:12]5[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=5[CH:4]3[C:5]2=[O:31])[C:10]2[CH:20]=[CH:21][CH:22]=[CH:23][C:9]4=2)[CH2:26][CH2:27][CH2:28][CH2:29][CH2:30]1

Participants

6

Reactant 4

HCID 241BenzeneHCID 5948TributylstannaneHCID 24408BromineHCID 20353281HCID 20353281, compound

Product 1

HCID 20353269HCID 20353269, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The above product (2.94 g) is treated with 1.41 g of bromine in methylene chloride at room temperature. The resulting crude 12b,13-dibromo-2-cyclohexylmethyl-2,3,8,12b-tetrahydro-1H-3a,8-methanodibenzo[3,4:6,7]cyclohepta[1,2-c]pyrrol-1-one is heated under reflux with 9 g of tributyltin hydride and 25 ml of anhydrous benzene for 3 days. The benzene is removed and the residue is concentrated further using short-path distillation (1 micron, 125° bath temperature). Crystallization of the residue from isopropyl alcohol gives 2.39 g of 2-cyclohexylmethyl-2,3,8,12b-tetrahydro-1H-3a,8-methanodibenzo[3,4:6,7]cyclohepta[1,2-c]pyrrol-1-one; nmr spectrum: τ 2.2-3.3 (m, 8); 5.9-6.2 (m, 2); 6.6-7.0 (m, 4); 8.1 (m, 2) and 8.1-9.7 (m, 11).

Workup

  1. customThe benzene is removed
  2. concentrationthe residue is concentrated further using
  3. distillationshort-path distillation (1 micron, 125° bath temperature)
  4. customCrystallization of the residue from isopropyl alcohol

Sources & evidence

ORD record
ord-030862f7cba24e71992394460f490d52
Source dataset
uspto-grants-1978_05
Patent number
US04088772

Reaction notes

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