Ammonia → (RS)-3-allyl-3-cyclopenten-1-yl 2,2,3,3-tetramethylcyclopropanecarboxylate

HRID 582735Notes

Reaction equation

HRID 582735 reaction equation
[CH2:1]([C:4]1[CH2:5][CH:6]([OH:9])[CH2:7][CH:8]=1)[CH:2]=[CH2:3].[CH3:10][C:11]1([CH3:19])[C:13]([CH3:15])([CH3:14])[CH:12]1[C:16](O)=[O:17].Cl.C(N=C=NCCCN(C)C)C.N>CN(C)C1C=CN=CC=1.ClCCl.C(N(CC)CC)C>[CH3:10][C:11]1([CH3:19])[C:13]([CH3:15])([CH3:14])[CH:12]1[C:16]([O:9][CH:6]1[CH2:7][CH:8]=[C:4]([CH2:1][CH:2]=[CH2:3])[CH2:5]1)=[O:17]

Participants

8

Reactant 4

HCID 222AmmoniaHCID 1521152,2,3,3-Tetramethylcyclopropanecarboxylic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 53659626(RS)-3-allyl-3-cyclopenten-1-ol

Product 1

HCID 54387663(RS)-3-allyl-3-cyclopenten-1-yl 2,2,3,3-tetramethylcyclopropanecarboxylateYield 8%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolventHCID 8471TriethylamineSolvent

Procedure

To a mixture of (RS)-3-allyl-3-cyclopenten-1-ol (300 mg), 2,2,3,3-tetramethylcyclopropanecarboxylic acid (343 mg), 4-dimethylaminopyridine (5 mg), triethylamine (733 mg) and dichloromethane (10 ml), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (WSC) was added under ice-cooling. The resulting reaction mixture was further allowed to react for 8 hours at room temperature. Then aqueous ammonia (10 ml) was added to the reaction mixture and the reaction mixture was stirred vigorously for 2 hours. The reaction solution was extracted twice with diethyl ether. After the combined ether layer was washed with saturated sodium chloride solution and dried over anhydrous magnesium sulfate, the solvent was evaporated under reduced pressure. The obtained residue was subjected to silica gel column chromatography to afford 45 mg of (RS)-3-allyl-3-cyclopenten-1-yl 2,2,3,3-tetramethylcyclopropanecarboxylate (Compound No. 117). Yield 8%

Workup

  1. additionwas added under ice-
  2. temperaturecooling
  3. customThe resulting reaction mixture
  4. customto react for 8 hours at room temperature
  5. extractionThe reaction solution was extracted twice with diethyl ether
  6. washAfter the combined ether layer was washed with saturated sodium chloride solution
  7. dry with materialdried over anhydrous magnesium sulfate
  8. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-205998eb801447d282754bb04b9fc447
Source dataset
uspto-grants-1999_07
Patent number
US05925676

Reaction notes

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