Water → HCID 23152338, compound

HRID 1012286Notes

Reaction equation

HRID 1012286 reaction equation
[CH:1]1([C:7]2[C:8]3[CH:25]=[CH:24][C:23]([C:26]([O:28][CH3:29])=[O:27])=[CH:22][C:9]=3[N:10]3[C:16]=2[C:15]2[CH:17]=[CH:18][C:19]([OH:21])=[CH:20][C:14]=2[O:13][CH2:12][CH2:11]3)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C1(C)C=CC(S(O[CH:40]2[CH2:45][CH2:44][CH2:43][N:42]([C:46]([O:48][C:49]([CH3:52])([CH3:51])[CH3:50])=[O:47])[CH2:41]2)(=O)=O)=CC=1.C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O>[C:49]([O:48][C:46]([N:42]1[CH2:43][CH2:44][CH2:45][CH:40]([O:21][C:19]2[CH:18]=[CH:17][C:15]3[C:16]4[N:10]([CH2:11][CH2:12][O:13][C:14]=3[CH:20]=2)[C:9]2[CH:22]=[C:23]([C:26]([O:28][CH3:29])=[O:27])[CH:24]=[CH:25][C:8]=2[C:7]=4[CH:1]2[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]2)[CH2:41]1)=[O:47])([CH3:52])([CH3:50])[CH3:51]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 11994998Methyl 12-cyclohexyl-3-hydroxy-6,7-dihydro-5-oxa-7a-azadibenzo[a,e]azulene-9-carboxylateHCID 20468243tert-Butyl 3-(tosyloxy)piperidine-1-carboxylate

Product 1

HCID 23152338HCID 23152338, compoundYield 58%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of methyl 12-cyclohexyl-3-hydroxy-6,7-dihydro-5-oxa-7a-azadibenzo[a,e]azulene-9-carboxylate (0.80 g, 2.04 mmol) in N,N-dimethylformamide (8 ml) were successively added tert-butyl 3-(toluene-4-sulfonyloxy)piperidine-1-carboxylate (1.09 g, 3.07 mmol) and potassium carbonate (0.57 g, 4.08 mmol) at room temperature, and the mixture was stirred overnight at 60° C. The reaction mixture was allowed to cool to room temperature, water was added to the reaction mixture and the mixture was extracted with ethyl acetate. The organic layer was successively washed with water and saturated brine and dried over anhydrous magnesium sulfate. After filtration, the solvent was concentrated under reduced pressure to give methyl 3-(1-tert-butoxycarbonylpiperidin-3-yloxy)-12-cyclohexyl-6,7-dihydro-5-oxa-7a-azadibenzo[a,e]azulene-9-carboxylate (0.68 g). The obtained compound was used for Step 3 without purification.

Workup

  1. customat room temperature
  2. temperatureto cool to room temperature
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe organic layer was successively washed with water and saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationAfter filtration
  7. concentrationthe solvent was concentrated under reduced pressure

Sources & evidence

ORD record
ord-d24b9c8e764747a9bb1a815967a15e69
Source dataset
uspto-grants-2011_07
Patent number
US07977331B1

Reaction notes

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