HCID 57857028, compound → HCID 57857042, compound

HRID 561760Notes

Reaction equation

HRID 561760 reaction equation
[C:1]([O:9][C@@H:10]1[CH2:18][C@@H:13]2[O:14][C:15](=[O:17])[CH2:16][C@@H:12]2[C@H:11]1/[CH:19]=[CH:20]/[C:21]([C:23]1[S:27][C:26]2[CH:28]=[CH:29][CH:30]=[CH:31][C:25]=2[CH:24]=1)=[O:22])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:32][Mg]Br>C1COCC1.C(OCC)C>[C:1]([O:9][C@@H:10]1[CH2:18][C@@H:13]2[O:14][C:15](=[O:17])[CH2:16][C@@H:12]2[C@H:11]1/[CH:19]=[CH:20]/[C:21]([C:23]1[S:27][C:26]2[CH:28]=[CH:29][CH:30]=[CH:31][C:25]=2[CH:24]=1)([OH:22])[CH3:32])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 57857028HCID 57857028, compound2×HCID 178418573HCID 178418573, compound

Product 1

HCID 57857042HCID 57857042, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-30 °C

Procedure

To a stirring solution consisting of (3aR,4R,5R,6aS)-4-((E)-3-(benzo[b]thiophen-2-yl)-3-oxoprop-1-enyl)-2-oxohexahydro-2H-cyclopenta[b]furan-5-yl benzoate (intermediate 4a prepared in Example 2, Step A) in THF (0.2 M) at −30° C. under a nitrogen atmosphere is slowly added a solution consisting of methylmagnesium bromide in diethyl ether (3 M, 1.5 molar equivalents). The reaction mixture is stirred at −30° C. until the reaction is complete as judged by TLC. Upon completion, the reaction mixture is warmed to 0° C. and is quenched with water and extracted into ethyl acetate. The layers are separated and the aqueous phase is extracted with a fresh portion of ethyl acetate. The organic layers are combined and dried over magnesium sulfate. The solvents are evaporated and the crude material is purified on regular silica gel eluted with an ethyl acetate-hexanes solvent system to afford the title intermediate.

Workup

  1. additionis slowly added a solution
  2. temperatureUpon completion, the reaction mixture is warmed to 0° C.
  3. customis quenched with water
  4. extractionextracted into ethyl acetate
  5. customThe layers are separated
  6. extractionthe aqueous phase is extracted with a fresh portion of ethyl acetate
  7. dry with materialdried over magnesium sulfate
  8. customThe solvents are evaporated
  9. customthe crude material is purified on regular silica gel
  10. washeluted with an ethyl acetate-hexanes solvent system

Sources & evidence

ORD record
ord-29ab780669904331a56b8cdd4b5e0ecd
Source dataset
uspto-grants-2011_11
Patent number
US08063240B2

Reaction notes

Loading…