Hydrochloric Acid → HCID 19079054, compound

HRID 1735852Notes

Reaction equation

HRID 1735852 reaction equation
[CH2:1]([C:4]1([CH2:19][CH2:20][N:21]2[CH2:25][CH2:24][CH2:23][CH:22]2[C:26]([O:28]C(C)(C)C)=[O:27])[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[CH2:8][CH2:7][C:6]2[CH:15]=[CH:16][CH:17]=[CH:18][C:5]1=2)[CH:2]=[CH2:3].Cl>C1COCC1.O1CCOCC1>[CH2:1]([C:4]1([CH2:19][CH2:20][N:21]2[CH2:25][CH2:24][CH2:23][CH:22]2[C:26]([OH:28])=[O:27])[C:5]2[CH:18]=[CH:17][CH:16]=[CH:15][C:6]=2[CH2:7][CH2:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]1=2)[CH:2]=[CH2:3]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 19079065HCID 19079065, compound

Product 1

HCID 19079054HCID 19079054, compoundYield 40%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 312751,4-DioxaneSolvent

Procedure

Dissolved 1,1-dimethylethyl 1-[2-[10,11-dihydro-5-(2-propenyl)-5H-dibenzo[a,d]cyclohepten-5-yl]ethyl]-2-pyrrolidinecarboxylate (2.40 g, 5.56 mmol) in 30 mL of dry THF. Added 25 mL of 4.0M HCl in dioxane, and refluxed for 16 hours on steam bath. Cooled to room temperature, and evaporated. Purified crude product by flash chromatography on silica gel eluting with 5% MeOH--CH2Cl2. Combined appropriate fractions and evaporated to give 0.80 g (40% yield) of 1-[2-[10,11-dihydro-5-(2-propenyl)-5H-dibenzo[a,d]cyclohepten-5-yl]ethyl]-2-pyrrolidinecarboxylic acid. Dissolved free base in dichloromethane, and added 3.4M HCl in ether to pH=2. Evaporated, and added ether to precipitate hydrochloride salt.

Workup

  1. temperaturerefluxed for 16 hours on steam bath
  2. customevaporated
  3. customPurified crude product by flash chromatography on silica gel eluting with 5% MeOH
  4. customevaporated

Sources & evidence

ORD record
ord-7603b0ff2c6c45b0abba32a6fe9c4d89
Source dataset
uspto-grants-1996_07
Patent number
US05538986

Reaction notes

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