Dichloromethane → HCID 10408278, compound

HRID 2181797Notes

Reaction equation

HRID 2181797 reaction equation
[C:1]([C@H:5]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[C:12]2[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=2[N:6]1[S:19]([C:22]1[CH:27]=[CH:26][C:25]([O:28]C)=[CH:24][CH:23]=1)(=[O:21])=[O:20])([CH3:4])([CH3:3])[CH3:2].C1CCCCC=1.B(Br)(Br)Br.ClCCl>>[C:1]([C@H:5]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[C:12]2[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=2[N:6]1[S:19]([C:22]1[CH:27]=[CH:26][C:25]([OH:28])=[CH:24][CH:23]=1)(=[O:21])=[O:20])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 4

HCID 6344DichloromethaneHCID 8079CyclohexeneHCID 25134Boron tribromideHCID 69354992HCID 69354992, compound

Product 1

HCID 10408278HCID 10408278, compound

Procedure

The title compound was prepared from (S)-6-tert-butyl-5-[(4-methoxyphenyl)sulfonyl]-5,6-dihydrophenanthridine (1.35 g, 3.31 mmol), cyclohexene (6.16 g, 75 mmol), and 1.0 M boron tribromide in dichloromethane (20 mL, 20 mmol) according to the procedure and in the same manner as described in Example 12, step b; and yielded, after chromatographic purification and crystallization from a mixture of diethyl ether-hexane, 4-{[(S)-6-tert-butylphenanthridin-5(6H)-yl]sulfonyl}phenol* (0.975 g, 2.48 mmol, 75%) as a homogeneous, colorless, crystalline (prisms), single enantiomer*, m.p. 187-189° C.;

Workup

  1. customand yielded
  2. customafter chromatographic purification and crystallization
  3. additionfrom a mixture of diethyl ether-hexane, 4-{[(S)-6-tert-butylphenanthridin-5(6H)-yl]sulfonyl}phenol* (0.975 g, 2.48 mmol, 75%) as a homogeneous, colorless, crystalline (prisms), single enantiomer*, m.p. 187-189° C.

Sources & evidence

ORD record
ord-8ff6067cd4c74bd8ba671710c425fea2
Source dataset
uspto-grants-2005_05
Patent number
US06894061B2

Reaction notes

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