Trimethylsilyldiazomethane → HCID 86606920, compound

HRID 747027Notes

Reaction equation

HRID 747027 reaction equation
[CH3:1][Si](C=[N+]=[N-])(C)C.[F:8][C:9]([F:39])([F:38])[C:10]1[CH:11]=[C:12]([C@H:20]([O:22][C@@H:23]2[C@@H:28]([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)[C@H:27]([C:35]([OH:37])=[O:36])[CH2:26][CH2:25][O:24]2)[CH3:21])[CH:13]=[C:14]([C:16]([F:19])([F:18])[F:17])[CH:15]=1>CO.C1(C)C=CC=CC=1>[F:39][C:9]([F:38])([F:8])[C:10]1[CH:11]=[C:12]([C@H:20]([O:22][C@@H:23]2[C@@H:28]([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)[C@H:27]([C:35]([O:37][CH3:1])=[O:36])[CH2:26][CH2:25][O:24]2)[CH3:21])[CH:13]=[C:14]([C:16]([F:17])([F:18])[F:19])[CH:15]=1

Participants

5

Reactant 2

HCID 167693TrimethylsilyldiazomethaneHCID 86606921HCID 86606921, compound

Product 1

HCID 86606920HCID 86606920, compoundYield 73%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 1140TolueneSolvent

Procedure

Trimethylsilyldiazomethane (2.0M in hexanes, 3.5 mL, 7 mmol) was added in portions over 1 hour to a solution of (2R,3R,4R)-2-{(1R)-1-[3,5-bis(trifluoromethyl)phenyl]ethoxy}tetrahydro-3-phenyl-2H-pyran-4-carboxylic acid (WO 00/56727A1; 3.2 g, 6.9 mmol) in a mixture of methanol (10 mL) and toluene (7 mL). The solvent was evaporated under reduced pressure and the residue was purified by column chromatography on silica gel, eluting with EtOAc/hexane (80:20), to give the title compound as a colorless solid (2.4 g, 73%).

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. customthe residue was purified by column chromatography on silica gel
  3. washeluting with EtOAc/hexane (80:20)

Sources & evidence

ORD record
ord-ba9d791352544e2f841c5e587ccc7860
Source dataset
uspto-grants-2008_07
Patent number
US07393858B2

Reaction notes

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