Triphenylphosphine → (S)-8-Fluoro-5-(4-methoxy-benzenesulfonyl)-6-methyl-5,6-dihydrophenanthridine

HRID 2224622Notes

Reaction equation

HRID 2224622 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[NH:14][S:15]([C:18]2[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[CH:20][CH:19]=2)(=[O:17])=[O:16])=[C:4]([C@H:26](O)[CH3:27])[CH:3]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CCOC(/N=N/C(OCC)=O)=O>O1CCCC1>[F:1][C:2]1[CH:3]=[C:4]2[C:5](=[CH:6][CH:7]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[N:14]([S:15]([C:18]1[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[CH:20][CH:19]=1)(=[O:17])=[O:16])[C@H:26]2[CH3:27]

Participants

5

Reactant 3

HCID 11776TriphenylphosphineHCID 5462977Diethyl azodicarboxylateHCID 69253499N-{4'-Fluoro-2'-[(R)-1-hydroxyethyl]-1,1'-biphenyl-2-yl}-4-methoxybenzenesulfonamide

Product 1

HCID 58597403(S)-8-Fluoro-5-(4-methoxy-benzenesulfonyl)-6-methyl-5,6-dihydrophenanthridineYield 79%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

N-{4′-fluoro-2′-[(1R)-1-hydroxyethyl]-1,1′-biphenyl-2-yl}-4-methoxybenzene-sulfonamide (0.12 g, 0.29 mmol) and triphenylphosphine (0.31 g, 1.2 mmol) were dissolved in tetrahydrofuran (10 mL) and diethylazodicarboxylate (0.21 g, 0.19 mL, 1.2 mmol) was added. The solution was stirred overnight at room temperature. The solution was concentrated in vacuo and the mixture was dissolved in ethyl acetate and washed with water. The organic phase was dried over anhydrous magnesium sulfate, filtered, and concentrated in vacuo. The crude product was purified by flash chromatography on silica gel (3:1 hexane: ethyl acetate) to yield the title compound as a crystalline solid (0.085 g, 79% ), m.p. 181-182° C.

Workup

  1. concentrationThe solution was concentrated in vacuo
  2. dissolutionthe mixture was dissolved in ethyl acetate
  3. washwashed with water
  4. dry with materialThe organic phase was dried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe crude product was purified by flash chromatography on silica gel (3:1 hexane: ethyl acetate)

Sources & evidence

ORD record
ord-90fdedd721a241f986fa99897b5f00d8
Source dataset
uspto-grants-2008_05
Patent number
US07378427B2

Reaction notes

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