HCID 18642346, compound → HCID 86746019, compound

HRID 655046Notes

Reaction equation

HRID 655046 reaction equation
[CH3:1][C@@:2]1([CH:13]=O)[C@H:9]2[CH2:10][C@H:5]([C@@H:6]([CH3:12])[C:7](=[O:11])[CH2:8]2)[O:4][O:3]1.[F:15][C:16]([F:52])([F:51])[C:17]1[CH:26]=[C:25]([C:27]2C=C[CH:30]=[CH:29][C:28]=2P(=C)(C2C=CC=CC=2)C2C=CC=CC=2)[C:24]2[C:19](=[CH:20][C:21]([C:47]([F:50])([F:49])[F:48])=[CH:22][CH:23]=2)[N:18]=1>C(Cl)Cl>[F:51][C:16]([F:15])([F:52])[C:17]1[CH:26]=[C:25](/[CH:27]=[CH:13]\[C@:2]2([CH3:1])[C@H:9]3[CH2:10][C@H:5]([C@@H:6]([CH3:12])[C:7](=[O:11])[CH2:8]3)[O:4][O:3]2)[C:24]2[C:19](=[CH:20][C:21]([C:47]([F:50])([F:48])[F:49])=[CH:22][CH:23]=2)[N:18]=1.[F:15][C:16]([F:52])([F:51])[C:17]1[CH:26]=[C:25](/[CH:27]=[CH:28]/[C@:29]2([CH3:30])[C@H:9]3[CH2:10][C@H:5]([C@@H:6]([CH3:12])[C:7](=[O:11])[CH2:8]3)[O:4][O:3]2)[C:24]2[C:19](=[CH:20][C:21]([C:47]([F:50])([F:49])[F:48])=[CH:22][CH:23]=2)[N:18]=1

Participants

5

Reactant 2

HCID 18642346HCID 18642346, compoundHCID 86746021HCID 86746021, compound

Product 2

HCID 86746019HCID 86746019, compoundHCID 86746020HCID 86746020, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

760 mg of (1R,4S,5S,8R)-4,8-dimethyl-7-oxo-2,3-dioxabicyclo[3.3.1]nonane-4-carboxaldehyde are dissolved in 80 ml of methylene chloride. 2.5 g of 2,7-bis(trifluoromethyl)quinolin-4-yl-methylidenetriphenylphosphorane are added thereto and the solution is left to stand at room temperature for 24 hours. The methylene chloride is distilled off and the residue is separated into the (E)- and (Z)-isomers by column chromatography on silica gel while eluting with methylene chloride. After crystallization from hot methanol there are obtained (1R,4S,5S,8R)-4-[(Z)-2-[2,7-bis(trifluoromethyl)-4-quinolinyl]vinyl]-4,8-dimethyl-2,3-dioxabicyclo[3.3.1]nonan-7-one as white crystals [m.p. 160°; [α]D25 =53.7° (c=1 in ethanol)] and (1R,4S,5S,8R)-4-[(E)-2-[2,7-bis(trifluoromethyl)-4-quinolinyl]vinyl]-4,8-dimethyl-2,3-dioxabicyclo[3.3.1]nonan-7-one [m.p. 188°].

Workup

  1. waitthe solution is left
  2. distillationThe methylene chloride is distilled off
  3. customthe residue is separated into the (E)- and (Z)-isomers by column chromatography on silica gel
  4. washwhile eluting with methylene chloride
  5. customAfter crystallization from hot methanol

Sources & evidence

ORD record
ord-9aa1b1975ba7457dbc11dc6af9254026
Source dataset
uspto-grants-1992_07
Patent number
US05134240

Reaction notes

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