Trimethylsilyldiazomethane → HCID 20638810, compound

HRID 1276514Notes

Reaction equation

HRID 1276514 reaction equation
[C:1]1([C@@H:7]2[CH:12]=[CH:11][CH2:10][CH2:9][C@@H:8]2[C:13]([OH:15])=[O:14])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:16][Si](C=[N+]=[N-])(C)C>CO.C1COCC1>[C:1]1([C@@H:7]2[CH:12]=[CH:11][CH2:10][CH2:9][C@@H:8]2[C:13]([O:15][CH3:16])=[O:14])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 167693TrimethylsilyldiazomethaneHCID 12633598HCID 12633598, compound

Product 1

HCID 20638810HCID 20638810, compound

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

To a solution of 900 mg (4.45 mmol) of 1(R)-phenyl-2(S)-carboxy cyclohex-5-ene (See U.S. Pat. No. 5,750,549, Example 158, Step B) in a 4:1 solution of MeOH/THF was added trimethylsilyldiazomethane until a yellow color persisted. After stirring at room temperature for 3 hour the reaction was concentrated in vacuo and the residue was purified by flash chromatography eluting with 0-15% EtOAc in hexanes to afford the ester (300 mg) as a colorless oil. 1H NMR (CDCl3, 500 MHz) δ 7.19-7.30 (m, 5H), 5.98-6.01 (m, 1H), 5.76-5.79 (m, 1H),3.89 (s, 1H),3.50 (s, 3H), 2.95-2.98 (m, 1H), 2.16-2.32 (m, 2H),1.80-1.87 (m, 2H) ppm.

Workup

  1. concentrationwas concentrated in vacuo
  2. customthe residue was purified by flash chromatography
  3. washeluting with 0-15% EtOAc in hexanes

Sources & evidence

ORD record
ord-a98d985ef2d146f692335e436761070f
Source dataset
uspto-grants-2000_12
Patent number
US06166037

Reaction notes

Loading…