p-Toluenesulfonic acid → HCID 57857065, compound

HRID 561732Notes

Reaction equation

HRID 561732 reaction equation
[F:1][C:2]([F:23])([CH2:15][O:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[CH2:3][CH2:4][C@@H:5]1[C@@H:12]2[C@@H:8]([O:9][C:10](=[O:13])[CH2:11]2)[CH2:7][C@H:6]1[OH:14].[O:24]1[CH:29]=[CH:28][CH2:27][CH2:26][CH2:25]1.C1(C)C=CC(S(O)(=O)=O)=CC=1>C(Cl)Cl.[Cl-].[Na+].O>[F:23][C:2]([F:1])([CH2:15][O:16][C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1)[CH2:3][CH2:4][C@@H:5]1[C@@H:12]2[C@@H:8]([O:9][C:10](=[O:13])[CH2:11]2)[CH2:7][C@H:6]1[O:14][CH:25]1[CH2:26][CH2:27][CH2:28][CH2:29][O:24]1

Participants

6

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 80803,4-dihydro-2H-pyranHCID 57857053HCID 57857053, compound

Product 1

HCID 57857065HCID 57857065, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

(3aR,4R,5R,6aS)-4-(3,3-Difluoro-4-phenoxybutyl)-5-hydroxyhexahydro-2H-cyclopenta[b]furan-2-one, prepared in Step D, is dissolved in DCM (0.1 M) under a nitrogen atmosphere. Dihydropyran (1.1 molar equivalents) is added, followed by a catalytic amount of p-toluenesulfonic acid. The reaction is stirred at room temperature under a nitrogen atmosphere and the reaction progress is monitored by TLC. Upon completion, brine is added to the reaction mixture and the layers are separated. The organic phase is dried over sodium sulfate, filtered, and the solvent is evaporated. The crude product is purified by flash chromatography on regular silica gel eluted with ethyl acetate-hexanes to afford the title intermediate.

Workup

  1. customthe layers are separated
  2. dry with materialThe organic phase is dried over sodium sulfate
  3. filtrationfiltered
  4. customthe solvent is evaporated
  5. customThe crude product is purified by flash chromatography on regular silica gel
  6. washeluted with ethyl acetate-hexanes

Sources & evidence

ORD record
ord-b7e60bec0cfd4269b0cac69691501a93
Source dataset
uspto-grants-2011_11
Patent number
US08063240B2

Reaction notes

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