Trimethylsilyldiazomethane → HCID 58626990, compound

HRID 983688Notes

Reaction equation

HRID 983688 reaction equation
[CH3:1][Si](C=[N+]=[N-])(C)C.[C:8]([O:12][C:13](=[O:25])[CH2:14][C@@:15]1([CH2:21][C:22]([OH:24])=[O:23])[CH2:19][CH2:18][C@@H:17]([CH3:20])[CH2:16]1)([CH3:11])([CH3:10])[CH3:9]>C1(C)C=CC=CC=1.CO>[C:8]([O:12][C:13](=[O:25])[CH2:14][C@@:15]1([CH2:21][C:22]([O:24][CH3:1])=[O:23])[CH2:19][CH2:18][C@@H:17]([CH3:20])[CH2:16]1)([CH3:9])([CH3:10])[CH3:11]

Participants

5

Reactant 2

HCID 167693TrimethylsilyldiazomethaneHCID 58626989HCID 58626989, compound

Product 1

HCID 58626990HCID 58626990, compoundYield 92.4%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 1140TolueneSolvent

Procedure

Trimethylsilyldiazomethane (14 mL of a 2 M solution in hexanes, 26.9 mmol) was added dropwise to a stirring solution of [(1S,3R)-1-carboxymethyl-3-methyl-cyclopentyl]-acetic acid tert-butyl ester (6.9 g, 26.9 mmol) in toluene (60 mL) and methanol (15 mL) at 10° C. under argon, and the mixture was allowed to warm to room temperature. The mixture was stirred for 2 hours, and then the solvent was evaporated under reduced pressure. The residue was taken up in ethyl acetate (200 mL), washed with saturated sodium hydrogen carbonate solution, dilute hydrochloric acid, dried (MgSO4), and the solvent removed in vacuo. The residue was purified by chromatography (silica gel, eluting with a gradient of heptane to 95:5 heptane:ethyl acetate) to give 6.73 g (92.4%) of [(1S,3R)-1-methoxycarbonylmethyl-3-methyl-cyclopentyl]-acetic acid tert-butyl 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
  5. customThe residue was purified by chromatography (silica gel
  6. washeluting with a gradient of heptane to 95:5 heptane

Sources & evidence

ORD record
ord-dc07c24beeff44bfb96173a4f84b86a2
Source dataset
uspto-grants-2005_03
Patent number
US06864390B2

Reaction notes

Loading…