Hydrochloric Acid → HCID 54424744, compound

HRID 1196657Notes

Reaction equation

HRID 1196657 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:12]3[CH2:13][CH2:14][CH2:15][CH:16]([C:18]([OH:20])=[O:19])[CH2:17][C:11]=3[O:10][N:9]=2)=[CH:4][CH:3]=1.[CH:21]([N-]C(C)C)(C)C.[Li+].C([Li])CCC.C(NC(C)C)(C)C.CI.Cl>O1CCCC1.CCCCCC.O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[C:12]3[CH2:13][CH2:14][CH2:15][C@@H:16]([C:18]([OH:20])=[O:19])[C@@H:17]([CH3:21])[C:11]=3[O:10][N:9]=2)=[CH:6][CH:7]=1

Participants

10

Reactant 6

HCID 313Hydrochloric AcidHCID 6328Methyl iodideHCID 7912DiisopropylamineHCID 2724682Lithium diisopropylamideHCID 19899000HCID 19899000, compoundHCID 178418339Butyllithium

Product 1

HCID 54424744HCID 54424744, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolvent

Conditions

Temperature
20 °C

Procedure

A solution of 1.46 g (0.005 mol) of 3-(4-chlorophenyl)-5,6,7,8-tetrahydro-4H-cyclohept[d]isoxazole-7-carboxylic acid in 20 ml of tetrahydrofuran was added slowly at -70° C. to a solution of lithium diisopropylamide prepared by adding 4.4 ml of a 2.5M solution of n-butyllithium in hexane to 1.11 g (0.011 mol) of diisopropylamine in 20 ml of dry tetrahydrofuran at -70° C. After 15 minutes, 0.78 g of methyl iodide was added and the mixture was allowed to warm to 20° C. The mixture was added to water, acidified with 2N hydrochloric acid and extracted with diethyl ether. The resulting mixture of the cis- and trans-3-(4-chlorophenyl)-5,6,7,8-tetrahydro-8-methyl-4H-cyclohept[d]isoxazole-7-carboxylic acid were separated by a combination of crystallization from acetic acid and chromatography on silica gel using toluene/methanol for the elution. There was obtained 0.4 g of cis-3-(4-chlorophenyl)-5,6,7,8-tetrahydro-8-methyl-4H-cyclohept[ d]isoxazole-7-carboxylic acid of melting point 230°-233° C. (from acetic acid).

Workup

  1. customprepared
  2. extractionextracted with diethyl ether
  3. additionThe resulting mixture of the cis- and trans-3-(4-chlorophenyl)-5,6,7,8-tetrahydro-8-methyl-4H-cyclohept[d]isoxazole-7-carboxylic acid
  4. customwere separated by a combination of crystallization from acetic acid and chromatography on silica gel
  5. washfor the elution

Sources & evidence

ORD record
ord-cea3d409f7ef41e2b81e46df5582816a
Source dataset
uspto-grants-1992_05
Patent number
US05114960

Reaction notes

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