Cyclohexene → HCID 10029985, compound

HRID 2181811Notes

Reaction equation

HRID 2181811 reaction equation
[CH:1]1[C:9]2[C:8]3[CH:10]=[CH:11][CH:12]=[CH:13][C:7]=3[O:6][C:5]=2[C:4]([C:14]2[CH:27]=[CH:26][C:25]3[N:24]([S:28]([C:31]4[CH:36]=[CH:35][C:34]([O:37]C)=[CH:33][CH:32]=4)(=[O:30])=[O:29])[CH:23]([CH2:39][CH3:40])[C:22]4[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=4)[C:16]=3[CH:15]=2)=[CH:3][CH:2]=1.C1CCCCC=1.B(Br)(Br)Br>ClCCl>[CH:1]1[C:9]2[C:8]3[CH:10]=[CH:11][CH:12]=[CH:13][C:7]=3[O:6][C:5]=2[C:4]([C:14]2[CH:27]=[CH:26][C:25]3[N:24]([S:28]([C:31]4[CH:32]=[CH:33][C:34]([OH:37])=[CH:35][CH:36]=4)(=[O:29])=[O:30])[CH:23]([CH2:39][CH3:40])[C:22]4[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=4)[C:16]=3[CH:15]=2)=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 8079CyclohexeneHCID 25134Boron tribromideHCID 22482358HCID 22482358, compound

Product 1

HCID 10029985HCID 10029985, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A stirred and cooled solution of 2-(dibenzo[b,d]furan-4-yl)-6-ethyl-5-[(4-methoxyphenyl)sulfonyl]-5,6-dihydrophenanthridine (0.855 g, 1.56 mmol) and cyclohexene (1.26 mL, 12.5 mmol) in dichloromethane (5 mL) was treated drop-wise under nitrogen at −30° C. with boron tribromide (1.18 mL, 12.5 mmol). After the addition was completed, the reaction mixture was allowed to warm to room temperature and stirred for four hours. The reaction was cooled to −30° C. and quenched with methanol (1 mL). The solvent was removed in vacuo, and the residue was purified by flash column chromatography on silica gel to yield the title compound (0.756 g, 1.42 mmol, 91%), which was characterized by LCMS (ES+, FA, CV=20 or 5), m.p. 218-220° C.;

Workup

  1. additionAfter the addition
  2. stirringstirred for four hours
  3. temperatureThe reaction was cooled to −30° C.
  4. customquenched with methanol (1 mL)
  5. customThe solvent was removed in vacuo
  6. customthe residue was purified by flash column chromatography on silica gel

Sources & evidence

ORD record
ord-f3786f06fdb34c468fefef0da786f43b
Source dataset
uspto-grants-2005_05
Patent number
US06894061B2

Reaction notes

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