Potassium Carbonate → HCID 86604442, compound

HRID 1858717Notes

Reaction equation

HRID 1858717 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[CH2:14][CH:13]3[N:15](C)[CH:10]([CH2:11][CH2:12]3)[CH:9]2[O:17][CH2:18][C:19]2[CH:28]=[CH:27][C:26]3[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=3)[CH:20]=2)=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].Cl[C:36]([O:38][CH2:39][C:40]([Cl:43])([Cl:42])[Cl:41])=[O:37]>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[CH2:14][CH:13]3[N:15]([C:36]([O:38][CH2:39][C:40]([Cl:43])([Cl:42])[Cl:41])=[O:37])[CH:10]([CH2:11][CH2:12]3)[CH:9]2[O:17][CH2:18][C:19]2[CH:28]=[CH:27][C:26]3[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=3)[CH:20]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 870632,2,2-Trichloroethyl chloroformateHCID 22128760HCID 22128760, compound

Product 1

HCID 86604442HCID 86604442, compoundYield 79.2%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

A solution of 1.02 g (2.6 mmol) of (1RS,2RS,3RS,5SR)-3-(4-chloro-phenyl)-8-methyl-2-(naphthalen-2-ylmethoxy)-8-aza-bicyclo[3.2.1]octane in 40 ml of toluene was treated with 150 mg of potassium carbonate and heated to 100° C. Subsequently, 0.635 g (0.400 ml) (3 mmol) of 2,2,2-trichloroethyl chloro-formate was added thereto and the mixture was stirred at 100° C. for 12 hours. The reaction solution was evaporated under reduced pressure, the residue was taken up in 70 ml of ethyl acetate and washed with 30 ml of water and 30 ml of saturated sodium hydrogen carbonate solution. Drying over magnesium sulphate, filtration and evaporation yielded a colourless oil which was chromatographed on silica gel using a 3:2 mixture of hexane and ethyl acetate. There were obtained 1.14 g (79% of theory) of 2,2,2-trichloroethyl (1RS,2RS,3RS,5SR)-3-(4-chloro-phenyl)-2-(naphthalen-2-ylmethoxy)-8-aza-bicyclo[3.2.1]octane-8-carboxylate as a colourless oil, Rf : 0.38 (silica gel, hexane:ethyl acetate=3:2).

Workup

  1. customThe reaction solution was evaporated under reduced pressure
  2. washwashed with 30 ml of water and 30 ml of saturated sodium hydrogen carbonate solution
  3. dry with materialDrying over magnesium sulphate, filtration and evaporation
  4. customyielded a colourless oil which
  5. customwas chromatographed on silica gel using
  6. additiona 3:2 mixture of hexane and ethyl acetate

Sources & evidence

ORD record
ord-841e36e0067c4d68b2f987bfdb87ca70
Source dataset
uspto-grants-2000_11
Patent number
US06150526

Reaction notes

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