Trimethylsilyldiazomethane → HCID 9878146, compound

HRID 983683Notes

Reaction equation

HRID 983683 reaction equation
[CH3:1][Si](C=[N+]=[N-])(C)C.[CH2:8]([C@:15]1([CH2:21][C:22]([OH:24])=[O:23])[CH2:19][CH2:18][C@@H:17]([CH3:20])[CH2:16]1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1>C1(C)C=CC=CC=1.CO>[CH3:1][O:23][C:22](=[O:24])[CH2:21][C@@:15]1([CH2:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH2:19][CH2:18][C@@H:17]([CH3:20])[CH2:16]1

Participants

5

Reactant 2

HCID 167693TrimethylsilyldiazomethaneHCID 58626983HCID 58626983, compound

Product 1

HCID 9878146HCID 9878146, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 1140TolueneSolvent

Procedure

Trimethylsilyldiazomethane (31.5 mL of a 2 M solution in hexanes, 63 mmol) was added dropwise to a stirring solution of ((1S,3R)-1-benzyl-3-methyl-cyclopentyl)-acetic acid (10 g, 43 mmol) in toluene (80 mL) and methanol (20 mL) at 0° C. under argon, and the mixture was allowed to warm to room temperature. The mixture was stirred for 1 hour, and then the solvent was evaporated under reduced pressure. The residue was taken up in ethyl acetate (50 mL), washed with saturated sodium hydrogen carbonate solution, dilute hydrochloric acid, dried (MgSO4), and the solvent removed in vacuo to give 10.6 g (100%) of ((1S,3R)-1-benzyl-3-methyl-cyclopentyl)-acetic acid methyl ester;

Workup

  1. customthe solvent was evaporated under reduced pressure
  2. washwashed with saturated sodium hydrogen carbonate solution, dilute hydrochloric acid
  3. dry with materialdried (MgSO4)
  4. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-80a2211a0bbf4e839e9e98fc9391abcc
Source dataset
uspto-grants-2005_03
Patent number
US06864390B2

Reaction notes

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